4-pyridinyl formamide compound or derivative thereof, preparation method therefor, herbicidal composition and use thereof

ABSTRACT

The invention belongs to the technical field of pesticides, and specifically relates to a 4-pyridinyl formamide compound or a derivative thereof, a preparation method therefor, a herbicidal composition and the use thereof. The 4-pyridinyl formamide compound is as represented by formula (I), wherein, X and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto, etc.; and M represents an unsubstituted or substituted structure (II). The compound, and the derivative and the composition thereof have excellent herbicidal activity and a higher crop safety, and establish good selectivity, especially for key crops such as wheat and rice.

TECHNICAL FIELD

The invention belongs to the technical field of pesticides, and specifically relates to a 4-pyridinyl formamide compound or derivative thereof, preparation method therefor, herbicidal composition and use thereof.

TECHNICAL BACKGROUND

Weed control is one of the most important links in the course of achieving high-efficiency agriculture. Various herbicides are available in the market, for example, WO2013087577A1 etc. disclose certain arylformamide compounds and their use as herbicides. However, due to the continuous expansion of the market, the resistance of weeds, the service life of chemicals and the economical efficiency of chemicals, as well as the increasing emphasis on the environment, especially the resistance of the mainstream ALS inhibitor and ACCe inhibitor herbicides is becoming more and more serious. In rice fields and wheat fields, more and more efficient, selective herbicides that can solve resistance are needed. This requires scientists to continuously research and develop new high-efficiency, safe, economic herbicides with different action modes.

Invention Contents

The present invention provides a 4-pyridinyl formamide compound or derivative thereof, preparation method therefor, herbicidal composition and use thereof. The compound has excellent herbicidal activity and a higher crop safety, and establishes good selectivity, especially for key crops such as wheat and rice.

The technical solution adopted by the invention is as follows:

A 4-pyridinyl formamide compound or derivative thereof, as shown in Formula I:

Wherein, X, and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, which is with or without halogen; OR¹, COR¹, COOR¹, OCOR¹, OCOOR¹, NR³SO₂R², OSO₂R², S(O)_(m)R², NR³COR¹, NR³COOR¹, C(O)NR³OR¹, SO₂OR¹, C(O)NR⁴R⁵, NR³C(O)NR⁴R⁵, OC(O)NR⁴R⁵, SO₂NR⁴R⁵, C(S)R¹, C(S)OR¹, C(S)SR², C(O)SR², SC(O)R¹, SC(S)R¹, OC(S)R¹, -alkyl-C(S)R¹, -alkyl-C(S)OR¹, -alkyl-C(O)SR¹, -alkyl-C(S)SR¹, -alkyl-SC(O)R¹, -alkyl-OC(S)R¹, -alkyl-SC(S)R¹, —O-alkyl-NR⁴R⁵, —S-alkyl-NR⁴R⁵, -alkyl-O-alkyl-NR⁴R⁵, -alkyl-S-alkyl-NR⁴R⁵, -alkyl-(C═S)_(n)—NR⁴R⁵, —NH-alkyl-NR⁴R⁵, -alkyl-OR¹, -alkyl-COR¹, -alkyl-CO₂R¹, -alkyl-OCOR¹, -alkyl-NR³COR¹, -alkyl-SO₂OR¹, -alkyl-NR³SO₂R², -alkyl-OSO₂R², -alkyl-S(O)_(m)R², -alkyl-CONR⁴R⁵, -alkyl-SO₂NR⁴R⁵, NR⁴R⁵,

P(O)(OR⁶)₂, CH₂P(O)(OR⁶)₂, SO₂NR⁴R⁵-alkyl-S(O)_(m)R², -alkyl-CN, -alkylaryl, -alkylheteroaryl, -alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl;

R¹, R³, R⁴, and R⁵ each independently represent hydrogen, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, halogenated alkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkyl, halogenated cycloalkyl, alkoxyalkyl, or cycloalkylalkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and alkoxyalkoxycarbonyl;

R² represents aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and alkoxyalkoxycarbonyl;

R⁶ represents methyl, or ethyl;

R⁷, and R⁸ each independently represent hydrogen, alkyl, alkenyl, or alkynyl;

R⁹ represents alkyl, alkenyl, or alkynyl;

M represents

which is unsubstituted or substituted;

R₁₁ represents hydrogen, halogen, cyano, nitro, alkyl which is unsubstituted or substituted with a substituent selected from R₁₃, cycloalkyl which is unsubstituted or substituted with a substituent selected from R₁₄, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, NH₂, aminoacyl, carboxyl, alkoxyalkoxycarbonyl, OR₁₅, -alkyl-OR₁₅, C(O)R₁₆, -alkyl-C(O)R₁₆, C(O)OR₁₆, -alkyl-C(O)OR₁₆, S(O)_(m)R₁₆, -alkyl-S(O)_(m)R₁₆, —N(R₁₆)₂, —NHR₁₆, —C(O)NHR₁₆, —C(O)N(R₁₆)₂, —NHC(O)Rn, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, arylalkyl, aryloxy, arylcarbonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, or heteroarylcarbonyl;

R₁₂ represents hydrogen, alkyl which is unsubstituted or substituted with a substituent selected from R₁₈, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylalkyl, aryl, or arylalkyl;

when M is

—(CH₂)₄— or —CH═CH—CH═CH— formed by R₁₁ and R₁₂, the nitrogen atom bound to R₁₂ and the carbon atom bound to R₁₁ together form a 6-membered ring;

R₁₅ represents alkyl which is unsubstituted or substituted with a substituent selected from R₂₁, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, or phenyl;

R₁₆ represents alkyl, halogenated alkyl, cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl;

R₂₁ represents halogen, cyano, cycloalkyl, hydroxy, mercapto, alkoxy, C(O)R₂₂, carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, —S(O)_(m)-alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with one or more groups selected from R₂₃;

R₁₇, and R₂₂ each independently represent hydrogen, alkyl, or N(R₂₄)R₂₅;

R₂₃ represents halogen, cyano, nitro, alkyl, alkyl which is unsubstituted or substituted with a substituent selected from R₃₁, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, alkylcarbonyl, cycloalkylcarbonyl, halogenated alkylcarbonyl, halogenated cycloalkylcarbonyl, alkoxycarbonyl, halogenated alkoxycarbonyl, alkylaminocarbonyl, halogenated alkylaminocarbonyl, bis(alkyl)aminocarbonyl, OR₃₂, S(O)_(m)R₃₃, alkylaminosulfonyl, bis(alkyl)aminosulfonyl, NH₂, alkylamino, bis(alkyl)amino, aryl, heteroaryl, or heterocyclyl;

R₂₄, and R₂₅ each independently represent hydrogen, alkyl, or phenyl; or,

alkylidene chain formed by R₂₄ and R₂₅, and the nitrogen atom(s) bound to R₂₄ and R₂₅ together form a 3-7-membered ring, said alkylidene chain optionally contains one O, S, S(O), S(O)₂, NH, or N-alkyl and optionally substituted by oxo or thio group;

R₁₃. R₁₄, R₁₈, and R₃₁ each independently represent halogen, cyano, nitro, carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, S(O)_(m)R₄₁, OR₄₂, aryl, heteroaryl, or heterocyclyl;

R₃₂ represents hydrogen, alkyl, halogenated alkyl, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl;

R₃₃ represents alkyl, halogenated alkyl, cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl;

R₄₁, and R₄₂ each independently represent hydrogen, alkyl, halogenated alkyl, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, or phenyl;

r represents 1 or 2;

m represents 0, 1 or 2;

n represents 0, or 1;

s represents 0, 1, 2 or 3.

Preferably, X, and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C6 alkyl, or C3-C8 cycloalkenyl-C1-C6 alkyl, which is with or without halogen; OR¹, COR¹, COOR¹, OCOR¹, OCOOR¹, NR³SO₂R², OSO₂R², S(O)_(m)R², NR³COR¹, NR³COOR¹, C(O)NR³OR¹, SO₂OR¹, C(O)NR⁴R⁵, NR³C(O)NR⁴R⁵, OC(O)NR⁴R⁵, SO₂NR⁴R⁵, C(S)R¹, C(S)OR¹, C(S)SR², C(O)SR², SC(O)R₂, SC(S)R¹, OC(S)R₁, —(C1-C6)alkyl-C(S)R¹, —(C1-C6)alkyl-C(S)OR¹, —(C1-C6)alkyl-C(O)SR¹, —(C1-C6)alkyl-C(S)SR¹, —(C1-C6)alkyl-SC(O)R¹, —(C1-C6)alkyl-OC(S)R¹, —(C1-C6)alkyl-SC(S)R¹, —O—(C1-C6)alkyl-NR⁴R⁵, —S—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-O—(C1-C6)alkyl-NR⁴R⁵,—(C1-C6)alkyl-S—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-(C═S)_(n)—NR⁴R⁵, —NH—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-OR¹, —(C1-C6)alkyl-COR¹, —(C1-C6)alkyl-CO₂R¹, —(C1-C6)alkyl-OCOR¹, —(C1-C6)alkyl-NR³COR¹, —(C1-C6)alkyl-SO₂OR¹, —(C1-C6)alkyl-NR³SO₂R², —(C1-C6)alkyl-OSO₂R², -alkyl-S(O)_(m)R², —(C1-C6)alkyl-CONR⁴R⁵, —(C1-C6)alkyl-SO₂NR⁴R⁵,NR⁴R⁵,

P(O)(OR⁶)₂, CH₂P(O)(OR⁶)₂, SO₂NR⁴R⁵—(C1-C6)alkyl-S(O)_(m)R², —(C1-C6)alkyl-CN, —(C1-C6)alkylaryl, —(C1-C6)alkylheteroaryl, —(C1-C6)alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl;

R¹, R³, R⁴, and R⁵ each independently represent hydrogen, aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkoxy-C1-C6 alkyl, or C3-C8 cycloalkyl-C1-C6 alkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C8 alkoxy-C1-C6 alkoxycarbonyl;

R² represents aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C6 alkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C8 alkoxy-C1-C6 alkoxycarbonyl;

R⁶ represents methyl, or ethyl;

R⁷, and R⁸ each independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl;

R⁹ represents C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl;

M represents

which is unsubstituted or substituted;

R₁₁ represents hydrogen, halogen, cyano, nitro, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₁₃, C3-C8 cycloalkyl which is unsubstituted or substituted with a substituent selected from R₁₄, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, NH₂, aminoacyl, carboxyl, C1-C8 alkoxy-C1-C6 alkoxycarbonyl, OR₁₅, —(C1-C6)alkyl-OR₁₅, C(O)R₁₆, —(C1-C6)alkyl-C(O)R₁₆, C(O)OR₁₆, —(C1-C6)alkyl-C(O)OR₁₆, S(O)_(m)R₁₆, —(C1-C6)alkyl-S(O)_(m)R₁₆, —N(R₁₆)₂, —NHR₁₆, —C(O)NHR₁₆, —C(O)N(R₁₆)₂, —NHC(O)Rn, heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, aryl-C1-C6 alkyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryl-C1-C6 alkyl, heteroaryloxy, or heteroarylcarbonyl;

R₁₂ represents hydrogen, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₁₈, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, C1-C8 alkoxy-C1-C6 alkyl, C1-C8 alkylthio-C1-C6 alkyl, C1-C8 alkoxycarbonyl-C1-C6 alkyl, aryl, or aryl-C1-C6 alkyl;

when M is

—(CH₂)₄— or —CH═CH—CH═CH— formed by R₁₁ and R₁₂, the nitrogen atom bound to R₁₂ and the carbon atom bound to R₁₁ together form a 6-membered ring;

R₁₅ represents C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₂₁, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or phenyl;

R₁₆ represents C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl;

R₂₁ represents halogen, cyano, C3-C8 cycloalkyl, hydroxy, mercapto, C1-C8 alkoxy, C(O)R₂₂, carboxyl, C1-C8 alkoxy carbonyl, C1-C8 alkoxy-C1-C6 alkoxy carbonyl, —S(O)_(m)—(C1-C8)alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with one or more groups selected from R₂₃;

R₁₇, and R₂₂ each independently represent hydrogen, C1-C8 alkyl, or N(R₂₄)R₂₅;

R₂₃ represents halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₃₁, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, C1-C8 alkylcarbonyl, C3-C8 cycloalkylcarbonyl, halogenated C1-C8 alkylcarbonyl, halogenated C3-C8 cycloalkylcarbonyl, C1-C8 alkoxy carbonyl, halogenated C1-C8 alkoxy carbonyl, C1-C8 alkylaminocarbonyl, halogenated C1-C8 alkylaminocarbonyl, bis(C1-C8 alkyl)aminocarbonyl, OR₃₂, S(O)_(m)R₃₃, C1-C8 alkylaminosulfonyl, bis(C1-C8 alkyl)aminosulfonyl, NH₂, C1-C8 alkylamino, bis(C1-C8 alkyl)amino, aryl, heteroaryl, or heterocyclyl;

R₂₄, and R₂₅ each independently represent hydrogen, C1-C8 alkyl, or phenyl; or,

C2-C8 alkylidene chain formed by R₂₄ and R₂₅, and the nitrogen atom(s) bound to R₂₄ and R₂₅ together form a 3-7-membered ring, said C2-C8 alkylidene chain optionally contains one O, S, S(O), S(O)₂, NH, or N-alkyl and optionally substituted by oxo or thio group;

R₁₃, R₁₄, R₁₈, and R₃₁ each independently represent halogen, cyano, nitro, carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy-C1-C8 alkoxy carbonyl, S(O)_(m)R₄₁, OR₄₂, aryl, heteroaryl, or heterocyclyl;

R₃₂ represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl;

R₃₃ represents C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl;

R₄₁, and R₄₂ each independently represent hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or phenyl;

r represents 1, or 2;

m represents 0, 1, or 2;

n represents 0, or 1;

s represents 0, 1, 2, or 3.

More preferably, X represents nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, or C3-C6 cycloalkenyl-C1-C3 alkyl, which is with or without halogen; OR¹, COR¹, COOR¹, OCOR¹, OCOOR¹, NR³SO₂R², OSO₂R², S(O)_(m)R², NR³COR¹, NR³COOR¹, C(O)NR³OR¹, SO₂OR¹, C(O)NR⁴R⁵, NR³C(O)NR⁴R⁵, OC(O)NR⁴R⁵, SO₂NR⁴R⁵, C(S)R¹, C(S)OR¹, C(S)SR², C(O)SR², SC(O)R¹, SC(S)R¹, OC(S)R¹, —(C1-C3)alkyl-C(S)R¹, —(C1-C3)alkyl-C(S)OR¹, —(C1-C3)alkyl-C(O)SR¹, —(C1-C3)alkyl-C(S)SR¹, —(C1-C3)alkyl-SC(O)R¹, —(C1-C3)alkyl-OC(S)R¹, —(C1-C3)alkyl-SC(S)R¹, —O—(C1-C3)alkyl-NR⁴R⁵, —S—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-O—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-S—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-(C═S)_(n)—NR⁴R⁵, —NH—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-OR¹, —(C1-C3)alkyl-COR¹, —(C1-C3)alkyl-CO₂R¹, —(C1-C3)alkyl-OCOR¹, —(C1-C3)alkyl-NR³COR¹, —(C1-C3)alkyl-SO₂OR¹, —(C1-C3)alkyl-NR³SO₂R², —(C1-C3)alkyl-OSO₂R², -alkyl-S(O)_(m)R², —(C1-C3)alkyl-CONR⁴R⁵, —(C1-C3)alkyl-SO₂NR⁴R⁵,NR⁴R⁵,

P(O)(OR⁶)₂, CH₂P(O)(OR⁶)₂, SO₂NR⁴R⁵—(C1-C3)alkyl-S(O)_(m)R², —(C1-C3)alkyl-CN, —(C1-C3)alkylaryl, —(C1-C3)alkylheteroaryl, —(C1-C3)alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl;

Y represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkenyl, which is with or without halogen; OR¹, S(O)_(m)R², NR⁴R⁵, heterocyclyl, aryl, or heteroaryl;

R¹, R³, R⁴, and R⁵ each independently represent hydrogen, aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, or C3-C6 cycloalkyl-C1-C3 alkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C6 alkoxy-C1-C3 alkoxycarbonyl;

R² represents aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C3 alkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C6 alkoxy-C1-C3 alkoxycarbonyl;

R⁶ represents methyl, or ethyl;

R⁷, and R⁸ each independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl,

R⁹ represents C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl;

M represents

which is unsubstituted or substituted;

R₁₁ represents hydrogen, halogen, cyano, nitro, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₁₃, C3-C6 cycloalkyl which is unsubstituted or substituted with a substituent selected from R₁₄, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, NH₂, aminoacyl, carboxyl, C1-C6 alkoxy-C1-C3 alkoxy carbonyl, OR₁₅, —(C1-C3)alkyl-OR₁₅, C(O)R₁₆, —(C1-C3)alkyl-C(O)R₁₆, C(O)OR₁₆, —(C1-C3)alkyl-C(O)OR₁₆, S(O)_(m)R₁₆, —(C1-C3)alkyl-S(O)_(m)R₁₆, —N(R₁₆)₂, —NHR₁₆, —C(O)NHR₁₆, —C(O)N(R₁₆)₂, —NHC(O)Rn, heterocyclyl, heterocyclyl-C1-C3 alkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, aryl-C1-C3 alkyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryl-C1-C3 alkyl, heteroaryloxy, or heteroarylcarbonyl;

R₁₂ represents hydrogen, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₁₈, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl, aryl, or aryl-C1-C3 alkyl;

when M is

—(CH₂)₄— or —CH═CH—CH═CH— formed by R₁₁ and R₁₂, the nitrogen atom bound to R₁₂ and the carbon atom bound to Rn together form a 6-membered ring;

R₁₅ represents C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₂₁, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, or phenyl;

R₁₆ represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl;

R₂₁ represents halogen, cyano, C3-C6 cycloalkyl, hydroxy, mercapto, C1-C6 alkoxy, C(O)R₂₂, carboxyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxy-C1-C3 alkoxy carbonyl, —S(O)_(m)—(C1-C6)alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with 1˜3 groups selected from R₂₃;

R₁₇, and R₂₂ each independently represent hydrogen, C1-C6 alkyl, or N(R₂₄)R₂₅;

R₂₃ represents halogen, cyano, nitro, C1-C6 alkyl, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₃₁, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, C1-C6 alkylcarbonyl, C3-C6 cycloalkylcarbonyl, halogenated C1-C6 alkylcarbonyl, halogenated C3-C6 cycloalkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated C1-C6 alkylaminocarbonyl, bis(C1-C6 alkyl)aminocarbonyl, OR₃₂, S(O)_(m)R₃₃, C1-C6 alkylaminosulfonyl, bis(C1-C6 alkyl)aminosulfonyl, NH₂, C1-C6 alkylamino, bis(C1-C6 alkyl)amino, aryl, heteroaryl, or heterocyclyl;

R₂₄, and R₂₅ each independently represent hydrogen, C1-C6 alkyl, or phenyl; or,

C2-C6 alkylidene chain formed by R₂₄ and R₂₅, and the nitrogen atom(s) bound to R₂₄ and R₂₅ together form a 3-7-membered ring, said C2-C6 alkylidene chain optionally contains one O, S, S(O), S(O)₂, NH, or N-alkyl and optionally substituted by oxo or thio group;

R₁₃, R₁₄, R₁₈, and R₃₁ each independently represent halogen, cyano, nitro, carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C6 alkoxy carbonyl, S(O)_(m)R₄₁, OR₄₂, aryl, heteroaryl, or heterocyclyl;

R₃₂ represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl;

R₃₃ represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl;

R₄₁, and R₄₂ each independently represent hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, or phenyl;

r represents 1, or 2;

m represents 0, 1, or 2;

n represents 0, or 1;

s represents 0, 1, 2, or 3.

Further preferably, X represents halogen, nitro, cyano, OR¹, S(O)_(m)R², NR COR¹. NR⁴R⁵,

C1-C6 alkoxy-C1-C3 alkyl; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, which is with or without halogen;

or phenyl which is unsubstituted or substituted with 1, 2, or 3 groups selected from halogen, and C1-C6 alkoxy;

Y represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkenyl, which is with or without halogen; OR¹, S(O)_(m)R², NR⁴R⁵, heterocyclyl, aryl, or heteroaryl;

R¹, R³, R⁴, and R⁵ each independently represent hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl; or benzyl which is unsubstituted or substituted with 1, 2, or 3 groups selected from halogen, and C1-C6 alkoxy;

R² represents C1-C6 alkyl, or halogenated C1-C6 alkyl;

M represents

which is unsubstituted or substituted;

R₁₁ represents hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, halogen, C1-C6 alkylamino, bis(C1-C6 alkyl)amino, cyano, nitro, C1-C6 alkylcarbonyl, C1-C6 alkoxy carbonyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl, aminocarbonyl, C1-C6 alkylcarbonylamino, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkylsulfinyl-C1-C3 alkyl, C1-C6 alkylsulfonyl-C1-C3 alkyl; or benzyl, phenoxy, benzoyl, pyridyl,

which is unsubstituted or substituted with 1, 2, or 3 groups selected from halogen, and C1-C6 alkoxy;

R₁₂ represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl; or phenyl, or benzyl which is unsubstituted or substituted with at least one group selected from halogen, and halogenated C1-C6 alkyl;

r represents 1, or 2;

m represents 0, 1, or 2;

wherein, the “heterocyclyl” is

the “aryl” is phenyl, naphthyl, or

which is unsubstituted or substituted; the “heteroaryl” is

which is unsubstituted or substituted; the aforementioned “substituted” respectively refers to being substituted by 1˜3 groups selected from: halogen, nitro, cyano, thiocyano, cyano C1-C3 alkyl, hydroxy, hydroxy C1-C3 alkyl, mercapto, carboxyl, formyl,

phenyl, phenyl substituted by C1-C6 alkyl, phenoxy, benzyloxy; amino, aminoalkyl, or aminocarbonyl group which is unsubstituted or substituted by one or two groups selected from C1-C6 alkyl, COR″, and COOR″; and C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkylcarbonylthio, C3-C6 cycloalkyl substituted with C1-C6 alkyl, OR″, SR″, SOR″, COR″, COOR″, or SO₂R″, which is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group, which is with or without halogen;

R′ each independently represents hydrogen, C1-C6 alkyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkyl,

C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C3 alkyl, or benzyl;

R″ each independently represents C1-C6 alkyl, or C2-C6 alkenyl.

Further preferably, X represents chlorine, fluorine, bromine, methyl, ethyl, isopropyl, vinyl, allyl, ethynyl, cyclopropyl, trifluoromethyl,

hydroxy, methoxy, ethyloxy, methylthio, ethylthio,

nitro, cyano, methylsulfinyl, ethylsulfinyl, methylsulfonyl, amino, monomethylamino, dimethylamino, acetamido,

phenyl, phenoxy, or 4-fluorophenyl;

Y represents methyl, ethyl, vinyl, methoxy,

phenoxy, benzyloxy, methylthio, propylthio, tert-butylthio, benzylthio, 4-methoxybenzylthiol, propylsulfinyl, amino, monomethylamino, dimethylamino, anilino, p-methoxybenzylamino, tert-butyl, cyclopropyl, cyclohexyl,

heterocyclyl, aryl, or heteroaryl;

M represents

which is unsubstituted or substituted;

R₁₁ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, monochloromethyl, trifluoromethyl, methoxy, isopropyloxy, methylthio, fluorine, chlorine, bromine, iodine, dimethylamino, ethylamino, cyano, nitro, acetyl, methoxycarbonyl; phenyl which is unsubstituted or substituted by 1, 2, or 3 groups selected from chlorine, and methoxy; pyridyl,

R₁₂ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, allyl,

or phenyl, or benzyl which is unsubstituted or substituted by 1,2, or 3 groups selected from chlorine, and trifluoromethyl;

r represents 1, or 2:

wherein, the “heterocyclyl” is

the “aryl” is phenyl, naphthyl, or

which is unsubstituted or substituted; the “heteroaryl” is

which is unsubstituted or substituted; the aforementioned “substituted” refers to being substituted by 1, 2, or 3 groups selected from: methyl, ethyl, isopropyl, n-butyl, tert-butyl, n-pentyl, vinyl, cyclopropyl,

fluorine, chlorine, bromine, iodine, monobromomethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy, trifluoromethoxy, hydroxyl, hydroxymethyl, amino, cyano, cyanomethyl, thiocyano, mercapto, nitro, carboxy, formyl, acetyl, methoxycarbonyl, tert-butyloxycarbonyl, methylthio, isopropylthio, methylsulfinyl, methylsulfonyl,

dimethylamino, aminocarbonyl, dimethylaminocarbonyl, acetylamino,

phenyl, 4-ethylphenyl, phenoxy, and benzyloxy; or, two adjacent substitutable positions of the above-mentioned “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group is with or without halogen;

R′ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, difluoromethyl, 3,3,3-trifluoroethyl, benzyl,

It should be particularly pointed out that when X is fluorine, Y is not amino, monomethylamino, monoethylamino and monopropylamino; when M is

X and Y are not methyl at the same time.

The structural formula of the derivative is

wherein Q represents hydrogen. -alkyl-Q₁, OQ₂, SQ₂, COQ₂, COOQ₂, CON(Q₃)₂, N(Q₃)₂, NQ₄COOQ₂, NQ₄CON(Q₃)₂; alkyl, alkenyl, alkynyl, or cycloalkyl, which is with or without halogen; or arylalkyl, or heteroarylalkyl, which is unsubstituted or substituted;

Q₁ each independently represents alkenyl, alkynyl, or cycloalkyl, which is with or without halogen; CN, OQ₁₁, OCOQ₁₁, COOQ₁₁, COQ₁₁, —O—(C═O)—O-Q₁₁, OSO₂Q₁₂, SO₂OQ₁₁, —S(O)_(p)Q₁₂, N(Q₁₃)₂, CON(Q₁₃)₂, SO₂N(Q₁₃)₂, NQ₁₄COQ₁₁, NQ₁₄SO₂Q₁₂, or —O—(C═O)—N(Q₁₃)₂;

Q₂, and Q₁₁ each independently represent hydrogen; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or alkoxyalkyl, which is with or without halogen; or heterocyclyl, heterocyclylalkyl, heterocyclyloxyalkyl, aryl, arylalkyl, aryloxyalkyl, heteroaryl, heteroarylalkyl, or heteroaryloxyalkyl, which is unsubstituted or substituted;

Q₁₂ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, or alkoxyalkyl, which is with or without halogen; or heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted;

Q₃, Q₄, Q₁₃, and Q₁₄ each independently represent hydrogen, nitro, alkoxyaminocarbonyl, trialkylsilyl, dialkylphosphonyl, N(Q₂₁)₂, CON(Q₂₁)₂, OQ₂₁, COQ₂₁, CO₂Q₂₁, COSQ₂₁, OCOQ₂₁, S(O)_(p)Q₂₂, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, halocycloalkyl, alkoxyalkyl, cycloalkylalkyl, aryl, arylalkyl, aryloxy, aryloxyalkyl, arylalkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, heteroaryloxyalkyl, heteroarylalkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclooxyalkyl, heterocyclylalkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NQ₂₁-alkyl, heteroaryl-NQ₂₁-alkyl, or heterocyclyl-NQ₂₁-alkyl, wherein the last 35 groups as mentioned each are independently substituted by 0, 1, 2, or 3 groups selected from the group consisting of cyano, halogen, nitro, cyanothio, OQ₂₁, S(O)_(p)Q₂₂, N(Q₂₁)₂, NQ₂₁OQ₂₁, COQ₂₁, OCOQ₂₁, SCOQ₂₂, NQ₂₁COQ₂₁, NQ₂₁SO₂Q₂₂, CO₂Q₂₁, COSQ₂₁, CON(Q₂₁)₂, and alkoxyalkoxy carbonyl;

Q₂₁ each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl;

Q₂₂ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl;

p each independently represents 0, 1, or 2.

Preferably, Q represents hydrogen, —(C1-C6)alkyl-Q₁, OQ₂, SQ₂, COQ₂, COOQ₂, CON(Q₃)₂, N(Q₃)₂, NQ₄COOQ₂, NQ₄CON(Q₃)₂; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, which is with or without halogen; or aryl-C1-C6 alkyl, or heteroaryl-C1-C6 alkyl, which is unsubstituted or substituted;

Q₁ each independently represents C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, which is with or without halogen; CN, OQ₁₁, OCOQ₁₁, COOQ₁₁, COQ₁₁, —O—(C═O)—O-Q₁₁, OSO₂Q₁₂, SC₂OQ₁₁, —S(O)_(p)Q₁₂, N(Q₁₃)₂, CON(Q₁₃)₂, SO₂N(Q₁₃)₂, NQ₁₄COQ₁₁, NQ₁₄SO₂Q₁₂, or —O—(C═O)—N(Q₁₃)₂;

Q₂, and Q₁₁ each independently represent hydrogen; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, or C1-C6 alkoxy-C1-C6 alkyl, which is with or without halogen; or heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, aryloxy-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, or heteroaryloxy-C1-C6 alkyl, which is unsubstituted or substituted;

Q₁₂ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl, or C1-C6 alkoxy-C1-C6 alkyl, which is with or without halogen; or heterocyclyl, heterocyclyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heteroaryl, or heteroaryl-C1-C6 alkyl, which is unsubstituted or substituted;

Q₃, Q₄, Q₁₃, and Q₁₄ each independently represent hydrogen, nitro, C1-C6 alkoxyaminocarbonyl, tri-C1-C6 alkylsilyl, di-C1-C6 dialkylphosphonyl, N(Q₂₁)₂, CON(Q₂₁)₂, OQ₂₁, COQ₂₁, CO₂Q₂₁, COSQ₂₁, OCOQ₂₁, S(O)_(p)Q₂₂, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 alkynyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, halo-C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C6 alkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, aryloxy, aryloxy-C1-C6 alkyl, aryl-C1-C6 alkyloxy, arylcarbonyl, arylsulfonyl, heteroaryl, heteroaryl-C1-C6 alkyl, heteroaryloxy, heteroaryloxy-C1-C6 alkyl, heteroaryl-C1-C6 alkyloxy, heteroarylcarbonyl, heteroarylsulfonyl, heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy, heterocyclooxy-C1-C6 alkyl, heterocyclyl-C1-C6 alkyloxy, heterocyclylcarbonyl, heterocyclylsulfonyl, aryl-NQ₂₁-(C1-C6)alkyl, heteroaryl-NQ₂₁-(C1-C6)alkyl, or heterocyclyl-NQ₂₁-(C1-C6)alkyl, wherein the last 35 groups as mentioned each are independently substituted by 0, 1, 2, or 3 groups selected from the group consisting of cyano, halogen, nitro, cyanothio, OQ₂₁, S(O)_(p)Q₂₂, N(Q₂₁)₂, NQ₂₁OQ₂₁, COQ₂₁, OCOQ₂₁, SCOQ₂₂, NQ₂₁COQ₂₁, NQ₂₁SO₂Q₂₂, CO₂Q₂₁, COSQ₂₁, CON(Q₂₁)₂, and C1-C6 alkoxy-C1-C6 alkoxycarbonyl;

Q₂₁ each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C6 alkyl;

Q₂₂ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C6 alkyl;

p each independently represents 0, 1, or 2.

In addition, the derivatives also include salts commonly used in pesticides, for example, it can be processed into an metal salt, an amine salt, a sulfonium salt or a phosphonium salt; or, when a basic moiety is present in the molecule, it can be processed into, for example, a sulfate, a hydrochloride, a nitrate, a phosphate, etc. When these salts are used as herbicides in agriculture or horticulture, they are also included in the present invention. In the present invention, the “metal salt” may be, for example, an alkali metal salt, an alkaline earth metal salt, an aluminum salt or an iron salt; the “alkali metal salt” may be, for example, a sodium salt, a potassium salt or a lithium salt, preferably a sodium salt or a potassium salt. In the present invention, the “alkaline earth metal salt” may be, for example, a calcium salt or a magnesium salt, preferably a calcium salt. In the present invention, the “amine salt” may be, for example, a secondary alkylamine salt, a tertiary alkylamine salt or a quaternary alkylammonium salt; a primary alkanolamine salt, a secondary alkanolamine salt, a tertiary alkanolamine salt or a quaternary alkanoammonium salt; a primary alkylalkanolamine salt, a secondary alkylalkanolamine salt, a tertiary alkylalkanolamine salt or a quaternary alkylalkanolammonium salt; or a primary alkoxyalkanolamine salt, a secondary alkoxyalkanolamine salt, a tertiary alkoxyalkanolamine salt or a quaternary alkoxyalkanolammonium salt, preferably, wherein the alkyl, alkanol and alkoxy are independently saturated and independently contain 1-4 carbon atoms, and may also be substituted by phenyl and/or halogen, more preferably, ethanolamine salt, dimethylethanolamine salt, triethanolamine salt, dimethylamine salt, triethylamine salt, isopropylamine salt, choline salt, diglycolamine salt,

In the present invention, the “sulfonium salt” and “phosphonium salt” may be, for example, an alkylsulfonium salt, an alkylphosphonium salt or an alkanolphosphonium salt, preferably, wherein the alkyl is independently saturated and independently contain 1-4 carbon atoms, and may also be substituted by phenyl and/or halogen, more preferably,

Solvates of the compounds of the invention are also included in the invention.

Wherein, unless otherwise specified, the “heterocyclyl” of the present invention includes but not limited to,

which has 0, 1 or 2 oxo groups; the “aryl” includes but not limited to, phenyl, naphthyl,

the “heteroaryl” is an aromatic cyclic group having, for example, 3 to 6 ring atoms and optionally fused with a benzo ring, 1 to 4 (for example, 1, 2, 3 or 4) of the ring atoms are heteroatoms (for example, oxygen, nitrogen and/or sulfur). For example,

the above-mentioned groups are respectively unsubstituted or substituted by at least one group selected from: halogen, nitro, cyano, thiocyano, cyanoalkyl, mercapto, hydroxy, hydroxyalkyl, carboxyl, formyl, trialkylsilyl, dialkylphosphonyl; heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkyl substituted by alkyl, OR″, SR″, -alkyl-OR″, —O-alkyl-OR″, -alkyl-SR″, COR″, -alkyl-COR″, —O-alkyl-COR″, COOR″, -alkyl-COOR″, —O-alkyl-COOR″, COSR″, SOR″, SO₂R″, —O—SO₂R″, -alkyl-SO₂R″, OCOR″, -alkyl-OCOR″, or SCOR″ group, which is with or without halogen; and amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, or aminosulfonyl group which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO₂R″, and OR″, wherein the R″, COR″, COOR″, SO₂R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O— or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O— or —CH═CH—CH═CH— group is with or without halogen;

R″ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl; or heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted.

Preferably, the above-mentioned groups are respectively unsubstituted or substituted by at least one group selected from: halogen, nitro, cyano, thiocyano, cyano C1-C6 alkyl, mercapto, hydroxy, hydroxy C1-C6 alkyl, carboxyl, formyl, tri(C1-C6 alkyl)silyl, di(C1-C6 alkyl)phosphonyl; heterocyclyl, heterocyclyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heteroaryl, or heteroaryl-C1-C6 alkyl, which is unsubstituted or substituted; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, OR″, SR″, —(C1-C6 alkyl)-OR″, —O—(C1-C6 alkyl)-OR″, —(C1-C6 alkyl)-SR″, COR″, —(C1-C6 alkyl)-COR″, —O—(C1-C6 alkyl)-COR″, COOR″, —(C1-C6 alkyl)-COOR″, —O—(C1-C6 alkyl) —COOR″, COSR″, SOR″, SO₂R″, —O—SO₂R″, —(C1-C6 alkyl)-SO₂R″, OCOR″, —(C1-C6 alkyl) —OCOR″, or SCOR″, which is with or without halogen; and amino, amino-C1-C6 alkyl, aminocarbonyl, aminocarbonyl-C1-C6 alkyl, or aminosulfonyl group, which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO₂R″, and OR″, wherein the R″, COR″, COOR″, SO₂R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group is with or without halogen;

R″ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl; or heterocyclyl, heterocyclyl-C1-C6 alkyl, aryl, aryl-C1-C6 alkyl, heteroaryl, or heteroaryl-C1-C6 alkyl, which is unsubstituted or substituted.

More preferably, the “heterocyclyl” is

which has 0, 1, or 2 oxo groups; the “aryl” is phenyl, naphthyl,

the “heteroaryl” is

the above-mentioned groups are respectively unsubstituted or substituted by 1˜3 groups selected from: halogen, nitro, cyano, thiocyano, cyano C1-C6 alkyl, mercapto, hydroxy, hydroxy C1-C6 alkyl, carboxyl, formyl;

phenyl, or benzyl group, which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxycarbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, OR″, SR″, —(C1-C6) alkyl —OR″, —O—(C1-C6) alkyl —OR″, —(C1-C6) alkyl —SR″, COR″, —(C1-C6) alkyl —COR″, —O—(C1-C6) alkyl —COR″, COOR″, —(C1-C6) alkyl —COOR″, —O—(C1-C6) alkyl —COOR″, COSR″, SOR″, SO₂R″, —O—SO₂R″, —(C1-C6) alkyl —SO₂R″, OCOR″, —(C1-C6) alkyl —OCOR″, or SCOR″ group, which is with or without halogen; and amino, aminoalkyl, aminocarbonyl, or aminosulfonyl group, which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO₂R″, and OR″, wherein the R″, COR″, COOR″, SO₂R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group is with or without halogen;

R′ each independently represents hydrogen, nitro, hydroxy, amino; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C6 alkyl,

C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxy carbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl-C1-C6 alkyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, C1-C6 alkylaminocarbonyl, C1-C6 alkoxyaminocarbonyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl, C1-C6 alkylaminocarbonyl-C1-C6 alkyl, tri(C1-C6 alkyl)silyl, or di(C1-C6 alkyl)phosphonyl, which is with or without halogen; or phenyl, or benzyl which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxy carbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen;

R″ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl; or

phenyl, or benzyl which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxy carbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen.

In the definition of the compound represented by the above Formula and all of the following structural formulas, the technical terms used, whether used alone or used in compound word, represent the following substituents: an alkyl having more than two carbon atoms may be linear or branched. For example, the alkyl in the compound word “-alkyl-OR¹” may be —CH₂—, —CH₂CH₂—, —CH(CH₃)—, —C(CH₃)₂—, and the like. The alkyl is, for example, C₁ alkyl; methyl; C₂ alkyl; ethyl; C₃ alkyl; propyl such as n-propyl or isopropyl; C₄ alkyl; butyl such as n-butyl, isobutyl, tert-butyl or 2-butyl; C₅ alkyl; pentyl such as n-pentyl; C₆ alkyl; hexyl such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, the alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, butyl-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. The alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bond(s) may be placed at any position of each unsaturated group. The cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, the cycloalkenyl is monocycloalkenyl having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bond can be at any position. Halogen is fluorine, chlorine, bromine or iodine.

If a group is substituted by a group, which should be understood to mean that the group is substituted by one or more groups, which are same or different groups, selected from the mentioned groups. In addition, the same or different substitution characters contained in the same or different substituents are independently selected, and may be the same or different. This is also applicable to ring systems formed with different atoms and units. Meanwhile, the scope of the claims will exclude those compounds chemically unstable under standard conditions known to those skilled in the art.

In addition, unless specifically defined, the term occurring after multiple juxtaposed substituents (separated by “,” or “or”) in the present invention has a limiting effect on each of the substituents, such as the term “with or without halogen” in “alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, which is with or without halogen” has a limiting effect on each of the following groups “alkyl”, “alkenyl”, “alkynyl”, “cycloalkyl”, “cycloalkenyl”, “cycloalkylalkyl” and “cycloalkenylalkyl”; a group (including heterocyclyl, aryl, heteroaryl, etc.) without being specified a linking site may be attached at any site, including a C or N site; if it is substituted, the substituent may be substituted at any site as long as it comply with the valence bond theory. For example, if the heteroaryl

is substituted with one methyl, it can be

etc.

Depending on the property of substituents and the linkage manner thereof, the compound of Formula I may exist as a stereoisomer. For example, if a compound has one or more asymmetric carbon atoms, it may has enantiomers and diastereomers. The stereoisomer can be obtained from the mixtures obtained in the preparation by conventional separation methods, for example by chromatographic separation. The stereoisomer may also be prepared selectively by using stereoselective reactions and using optically active starting materials and/or auxiliaries. The present invention also relates to all stereoisomers and mixtures thereof which are included in the general Formula I but are not specifically defined.

A method for preparing the 4-pyridinyl formamide compound I, which comprises the following steps:

subjecting the compound of the general formula II and the compound of the general formula III to amidation reaction to obtain the compound of the general formula I, the chemical reaction scheme is as follows:

The reaction is carried out in the presence of a halogenating agent, a catalyst and a solvent; preferably, the halogenating agent is SOCl₂, the catalyst is 4-dimethylaminopyridine, and the solvent is pyridine;

Or the reaction is carried out in the presence of a condensing agent and a solvent; preferably, the condensing agent is CDI, DCC, DBU or a combination thereof, and the solvent is methylene chloride.

The preparation method of its derivative 1-1 includes the following steps:

subjecting the compound of the general formula I and Hal-Q to reaction to obtain the compound of the general formula I-1, the chemical reaction scheme is as follows:

Wherein, Hal represents halogen, preferably fluorine, chlorine or bromine;

The reaction is carried out in the presence of a base and a solvent; preferably, the base is selected from one or a combination of potassium carbonate and sodium carbonate, and the solvent is one or more selected from the group consisting of DCM, DCE, ACN, THF, and DMF; or the reaction is carried out in the presence of a catalyst and a solvent; preferably, the catalyst is 4-dimethylaminopyridine, and the solvent is pyridine.

In addition, the compound of the general formula II and the compound of the general formula III are known in principle, and can be prepared, for example, by the methods described in WO199835967A2, CN103459386A, CN103987701A, WO2017055146A, WO2013017559A1, WO2012028579A1, WO2011035874A1. Moreover, the compounds of the present invention can also be prepared by referring to the methods described therein.

A herbicidal composition comprising (i) the 4-pyridinyl formamide compound or derivative thereof as shown in general formula I; preferably, further comprising (ii) one or more further herbicides and/or safeners; more preferably, further comprising (iii) agrochemically acceptable formulation auxiliaries.

A method for controlling a weed which comprises applying a herbicidally effective amount of at least one of the 4-pyridinyl formamide compound or derivative thereof or the herbicidal composition as above-described to a plant or a weed area.

Use of at least one of the 4-pyridinyl formamide compound or derivative thereof or the herbicidal composition as above-described for controlling a weed, preferably, wherein the 4-pyridinyl formamide compound or derivative thereof is used for preventing and/or controlling a weed in a useful crop, wherein the useful crop is a transgenic crop or a crop treated by gene editing technique.

The compounds of the formula I according to the invention have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. The active compounds also act efficiently on perennial weeds which produce shoots from rhizomes, root stocks or other perennial organs and which are difficult to control. In this context, it is generally immaterial whether the substances are applied pre-sowing, pre-emergence or post-emergence. Specifically, examples may be mentioned of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention, without these being a restriction to certain species. Examples of weed species on which the active compounds act efficiently are, from amongst the monocotyledons, Avena, Lolium, Alopecurus, Phalaris, Echinochloa, Digitaria, Setaria and also Cyperus species from the annual sector and from amongst the perennial species Agropyron, Cynodon, Imperata and Sorghum, and also perennial Cyperus species.

In the case of the dicotyledonous weed species, the spectrum of action extends to species such as, for example, Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Sida, Matricaria and Abutilon from amongst the annuals, and Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial weeds. The active compounds according to the invention also effect outstanding control of harmful plants which occur under the specific conditions of rice growing such as, for example, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus. If the compounds according to the invention are applied to the soil surface prior to germination, then the weed seedlings are either prevented completely from emerging, or the weeds grow until they have reached the cotyledon stage but then their growth stops, and, eventually, after three to four weeks have elapsed, they die completely. In particular, the compounds according to the invention exhibit excellent activity against Apera spica venti, Chenopodium album, Lamium purpureum, Polygonum convulvulus, Stellaria media, Veronica hederifolia, Veronica persica, Viola tricolor and against Amaranthus, Galium and Kochia species.

Although the compounds according to the invention have an excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops such as, for example, wheat, barley, rye, rice, corn, sugarbeet, cohon and soya, are not damaged at all, or only to a negligible extent. In particular, they have excellent compatibility in cereals, such as wheat, barley and corn, in particular wheat. For these reasons, the present compounds are highly suitable for selectively controlling undesired plant growth in plantings for agricultural use or in plantings of ornamentals.

Owing to their herbicidal properties, these active compounds can also be employed for controlling harmful plants in crops of known or still to be developed genetically engineered plants. The transgenic plants generally have particularly advantageous properties, for example resistance to certain pesticides, in particular certain herbicides, resistance to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the quantity, quality, storage-stability, composition and to specific ingredients of the harvested product. Thus, transgenic plants having an increased starch content or a modified quality of the starch or those having a different fatty acid composition of the harvested produce are known.

The use of the compounds of the formula I according to the invention or their derivatives in economically important transgenic crops of useful and ornamental plants, for example of cereal, such as wheat, barley, rye, oats, millet, rice, maniok and corn, or else in crops of sugarbeet, cotton, soya, rapeseed, potato, tomato, pea and other vegetable species is preferred. The compounds of the formula I can preferably be used as herbicides in crops of useful plants which are resistant or which have been made resistant by genetic engineering toward the phytotoxic effects of the herbicides.

Conventional ways for preparing novel plants which have modified properties compared to known plants comprise, for example, traditional breeding methods and the generation of mutants. Alternatively, novel plants having modified properties can be generated with the aid of genetic engineering methods (see, for example, EP-A0 221 044, EP-A0 131 624). For example, there have been described several cases of:

-   -   genetically engineered changes in crop plants in order to modify         the starch synthesized in the plants (for example WO 92/11376,         WO 92/14827, WO 91/19806),     -   transgenic crop plants which are resistant to certain herbicides         of the glufosinate- (cf., for example, EP-A 0 242 236, EP-A 0         242 246) or glyphosate-type (WO 92/00377), or of the         sulfonylurea-type (EP-A0 257 993, U.S. Pat. No. 5,013,659A),     -   transgenic crop plants, for example cohon, having the ability to         produce Bacillus thuringiensis toxins (Bt toxins) which impart         resistance to certain pests to the plants (EP-A 0 142 924, EP-A0         193 259),     -   transgenic crop plants having a modified fatty acid composition         (WO 91/13972).

Numerous molecular biological techniques which allow the preparation of novel transgenic plants having modified properties are known in principle; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone” [Genes and Clones], VCH Weinheim, 2nd edition 1996, or Christou, “Trends in Plant Science” 1 (1996) 423-431). In order to carry out such genetic engineering manipulations, it is possible to introduce nucleic acid molecules into plasmids which allow a mutagenesis or a change in the sequence to occur by recombination of DNA sequences. Using the abovementioned standard processes it is possible, for example, to exchange bases, to remove partial sequences or to add natural or synthetic sequences. To link the DNA fragments with each other, it is possible to attach adaptors or linkers to the fragments.

Plant cells having a reduced activity of a gene product can be prepared, for example, by expressing at least one appropriate antisense-RNA, a sense-RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product.

To this end it is possible to employ both DNA molecules which comprise the entire coding sequence of a gene product including any flanking sequences that may be present, and DNA molecules which comprise only parts of the coding sequence, it being necessary for these parts to be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but which are not entirely identical.

When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of the plant cells. However, to achieve localization in a certain compartment, it is, for example, possible to link the coding region with DNA sequences which ensure localization in a certain compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

The transgenic plant cells can be regenerated to whole plants using known techniques. The transgenic plants can in principle be plants of any desired plant species, i.e. both monocotyledonous and dicotyledonous plants. In this manner, it is possible to obtain transgenic plants which have modified properties by overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or by expression of heterologous (=foreign) genes or gene sequences.

When using the active compounds according to the invention in transgenic crops, in addition to the effects against harmful plants which can be observed in other crops, there are frequently effects which are specific for the application in the respective transgenic crop, for example a modified or specifically broadened spectrum of weeds which can be controlled, modified application rates which can be used for the application, preferably good combinability with the herbicides to which the transgenic crops are resistant, and an effect on the growth and the yield of the transgenic crop plants. The invention therefore also provides for the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

In addition, the substances according to the invention have outstanding growth-regulating properties in crop plants. They engage in the plant metabolism in a regulating manner and can this be employed for the targeted control of plant constituents and for facilitating harvesting, for example by provoking desiccation and stunted growth. Furthermore, they are also suitable for generally regulating and inhibiting undesirable vegetative growth, without destroying the plants in the process. Inhibition of vegetative growth plays an important role in many monocotyledon and dicotyledon crops because lodging can be reduced hereby, or prevented completely.

The compounds according to the invention can be applied in the customary formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also provides herbicidal compositions comprising compounds of the formula I. The compounds of the formula I can be formulated in various ways depending on the prevailing biological and/or chemico-physical parameters. Examples of suitable formulation options are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil dispersions (OD), oil- or water-based dispersions, oil-miscible solutions, dusts (DP), capsule suspensions (CS), seed-dressing compositions, granules for broadcasting and soil application, granules (GR) in the form of microgranules, spray granules, coating granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in Winnacker-Kiichler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th. Edition 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The necessary formulation auxiliaries, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, “Grenzfliichenaktive Athylenoxidaddkte” [Surface-active ethylene oxide adducts], Wiss. Verlagagesell. Stuttgart 1976; Winnacker-Kiichler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th Edition 1986.

Wettable powders are preparations which are uniformly dispersible in water and which contain, in addition to the active compound and as well as a diluent or inert substance, surfactants of ionic and/or nonionic type (wetting agents, dispersants), for example polyethoxylated alkyl phenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ethersulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutyinaphthalenesulfona-te or else sodium oleoylmethyltaurinate. To prepare the wettable powders, the herbicidally active compounds are finely ground, for example in customary apparatus such as hammer mills, fan mills and air-jet mills, and are mixed simultaneously or subsequently with the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else relatively high-boiling aromatic compounds or hydrocarbons or mixtures of the solvents, with the addition of one or more surfactants of ionic and/or nonionic type (emulsifiers). Examples of emulsifiers which can be used are calcium alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth. Suspension concentrates can be water- or oil-based. They can be prepared, for example, by wet milling using commercially customary bead mills, with or without the addition of surfactants as already mentioned above, for example, in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if desired, surfactants as already mentioned above, for example, in the case of the other formulation types.

Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or by applying active-compound concentrates to the surface of carriers such as sand, kaolinites or granulated inert material, by means of adhesive binders, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active compounds can also be granulated in the manner which is customary for the preparation of fertilizer granules, if desired as a mixture with fertilizers. Water-dispersible granules are generally prepared by the customary processes, such as spray-drying, fluidized-bed granulation, disk granulation, mixing using high-speed mixers, and extrusion without solid inert material.

For the preparation of disk, fluidized-bed, extruder and spray granules, see for example processes in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57. For further details on the formulation of crop protection products, see for example G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula F In wettable powders the concentration of active compound is, for example, from about 10 to 99% by weight, the remainder to 100% by weight consisting of customary formulation constituents. In emulsifiable concentrates the concentration of active compound can be from about 1 to 90%, preferably from 5 to 80%, by weight. Formulations in the form of dusts contain from 1 to 30% by weight of active compound, preferably most commonly from 5 to 20% by weight of active compound, while sprayable solutions contain from about 0.05 to 80%, preferably from 2 to 50%, by weight of active compound. In the case of water-dispersible granules the content of active compound depends partly on whether the active compound is in liquid or solid form and on the granulation auxiliaries, fillers, etc. that are used. In water-dispersible granules the content of active compound, for example, is between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the formulations of active compound may comprise the tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and pH and viscosity regulators which are customary in each case.

Based on these formulations it is also possible to produce combinations with other pesticidally active substances, for example insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers and/or growth regulators, for example in the form of a ready-mix or tank mix.

Suitable active compounds which can be combined with the active compounds according to the invention in mixed formulations or in a tank mix are, for example, known active compounds as described in for example World Herbicide New Product Technology Handbook, China Agricultural Science and Farming Techniques Press, 2010.9 and in the literature cited therein. For example the following active compounds may be mentioned as herbicides which can be combined with the compounds of the formula I (note: the compounds are either named by the “common name” in accordance with the International Organization for Standardization (ISO) or by the chemical names, if appropriate together with a customary code number): acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propachlor, ethachlor, napropamide, R-left handed napropamide, propanil, mefenacet, diphenamid, diflufenican, ethaprochlor, beflubutamid, bromobutide, dimethenamid, dimethenamid-P, etobenzanid, flufenacet, thenylchlor, metazachlor, isoxaben, flamprop-M-methyl, flamprop-M-propyl, allidochlor, pethoxamid, chloranocryl, cyprazine, mefluidide, monalide, delachlor, prynachlor, terbuchlor, xylachlor, dimethachlor, cisanilide, trimexachlor, clomeprop, propyzamide, pentanochlor, carbetamide, benzoylprop-ethyl, cyprazole, butenachlor, tebutam, benzipram, mogrton, dichlofluanid, naproanilide, diethatyl-ethyl, naptalam, flufenacet, EL-177, benzadox, chlorthiamid, chlorophthalimide, isocarbamide, picolinafen, atrazine, simazine, prometryn, cyanatryn, simetryn, ametryn, propazine, dipropetryn, SSH-108, terbutryn, terbuthylazine, triaziflam, cyprazine, proglinazine, trietazine, prometon, simetone, aziprotryne, desmetryn, dimethametryn, procyazine, mesoprazine, sebuthylazine, secbumeton, terbumeton, methoprotryne, cyanatryn, ipazine, chlorazine, atraton, pendimethalin, eglinazine, cyanuric acid, indaziflam, chlorsulfuron, metsulfuron-methyl, bensulfuron methyl, chlorimuron-ethyl, tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, mesosulfuron, iodosulfuron-methyl sodium, foramsulfuron, cinosulfuron, triasulfuron, sulfometuron methyl, nicosulfuron, ethametsulfuron-methyl, amidosulfuron, ethoxy sulfur on, cyclosulfamuron, rimsulfuron, azimsulfuron, flazasulfuron, monosulfuron, monosulfuron-ester, flucarbazone-sodium, flupyrsulfuron-methyl, halosulfuron-methyl, oxasulfuron, imazosulfuron, primisulfuron, propoxycarbazone, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron, sodium metsulfuron methyl, flucetosulfuron, HNPC—C, orthosulfamuron, propyrisulfuron, metazosulfuron, acifluorfen, fomesafen, lactofen, fluoroglycofen, oxyfluorfen, chlomitrofen, aclonifen, ethoxyfen-ethyl, bifenox, nitrofluorfen, chlomethoxyfen, fluorodifen, fluoronitrofen, furyloxyfen, nitrofen, TOPE, DMNP, PPG1013, AKH-7088, halosafen, chlortoluron, isoproturon, linuron, diuron, dymron, fluometuron, benzthiazuron, methabenzthiazuron, cumyluron, ethidimuron, isouron, tebuthiuron, buturon, chlorbromuron, methyldymron, phenobenzuron, SK-85, metobromuron, metoxuron, afesin, monuron, siduron, fenuron, fluothiuron, neburon, chloroxuron, noruron, isonoruron, 3-cyclooctyl-1, thiazfluron, tebuthiuron, difenoxuron, parafluron, methylamine tribunil, karbutilate, trimeturon, dimefuron, monisouron, anisuron, methiuron, chloreturon, tetrafluron, phenmedipham, phenmedipham-ethyl, desmedipham, asulam, terbucarb, barban, propham, chlorpropham, rowmate, swep, chlorbufam, carboxazole, chlorprocarb, fenasulam, BCPC, CPPC, carbasulam, butylate, benthiocarb, vemolate, molinate, triallate, dimepiperate, esprocarb, pyributicarb, cycloate, avadex, EPTC, ethiolate, orbencarb, pebulate, prosulfocarb, tiocarbazil, CDEC, dimexano, isopobnate, methiobencarb, 2,4-D butyl ester, MCPA-Na, 2,4-D isooctyl ester, MCPA isooctyl ester, 2,4-D sodium salt, 2,4-D dimethyla mine salt, MCPA-thioethyl, MCPA, 2,4-D propionic acid, high 2,4-D propionic acid salt, 2,4-D butyric acid, MCPA propionic acid, MCPA propionic acid salt, MCPA butyric acid, 2,4,5-D, 2,4,5-D propionic acid, 2,4,5-D butyric acid, MCPA amine salt, dicamba, erbon, chlorfenac, saison, TBA, chloramben, methoxy-TBA, diclofop-methyl, fluazifop-butyl, fluazifop-p-butyl, haloxyfop-methyl, haloxyfop-P, quizalofop-ethyl, quizalofop-p-ethyl, fenoxaprop-ethy, fenoxaprop-p-ethyl, propaquizafop, cyhalofop-butyl, metamifop, clodinafop-propargyl, fenthiaprop-ethyl, chloroazifop-propynyl, poppenate-methyl, trifopsime, isoxapyrifop, paraquat, diquat, oryzalin, ethalfluralin, isopropalin, nitralin, profluralin, prodinamine, benfluralin, fluchloraline, dinitramina, dipropalin, chlomidine, methalpropalin, dinoprop, glyphosate, anilofos, glufosinate ammonium, amiprophos-methyl, sulphosate, piperophos, bialaphos-sodium, bensulide, butamifos, phocarb, 2,4-DEP, H-9201, zytron, imazapyr, imazethapyr, imazaquin, imazamox, imazamox ammonium salt, imazapic, imazamethabenz-methyl, fluroxypyr, fluroxypyr isooctyl ester, clopyralid, picloram, trichlopyr, dithiopyr, haloxydine, 3,5,6-trichloro-2-pyridinol, thiazopyr, fluridone, aminopyralid, diflufenzopyr, triclopyr-butotyl, Cliodinate, sethoxydim, clethodim, cycloxydim, alloxydim, clefoxydim, butroxydim, tralkoxydim, tepraloxydim, buthidazole, metribuzin, hexazinone, metamitron, ethiozin, ametridione, amibuzin, bromoxynil, bromoxynil octanoate, ioxynil octanoate, ioxynil, dichlobenil, diphenatrile, pyraclonil, chloroxynil, iodobonil, flumetsulam, florasulam, penoxsulam, metosulam, cloransulam-methyl, diclosulam, pyroxsulam, benfuresate, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, benzobicylon, mesotrione, sulcotrione, tembotrione, tefuryltrione, bicyclopyrone, ketodpiradox, isoxaflutole, clomazone, fenoxasulfone, methiozolin, fluazolate, pyraflufen-ethyl, pyrazolynate, difenzoquat, pyrazoxyfen, benzofenap, nipyraclofen, pyrasulfotole, topramezone, pyroxasulfone, cafenstrole, flupoxam, aminotriazole, amicarbazone, azafenidin, carfentrazone-ethyl, sulfentrazone, bencarbazone, benzfendizone, butafenacil, bromacil, isocil, lenacil, terbacil, flupropacil, cinidon-ethyl, flumiclorac-pentyl, flumioxazin, propyzamide, MK-129, flumezin, pentachlorophenol, dinoseb, dinoterb, dinoterb acetate, dinosam, DNOC, chloronitrophene, medinoterb acetate, dinofenate, oxadiargyl, oxadiazon, pentoxazone, Flufenacet, fluthiacet-methyl, fentrazamide, flufenpyr-ethyl, pyrazon, brompyrazon, metflurazon, kusakira, dimidazon, oxapyrazon, norflurazon, pyridafol, quinclorac, quinmerac, bentazone, pyridate, oxaziclomefone, benazolin, clomazone, cinmethylin, ZJ0702, pyribambenz-propyl, indanofan, sodium chlorate, dalapon, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, flupropanate, cyperquat, bromofenoxim, epronaz, methazole, flurtamone, benfuresate, ethofumesate, tioclorim, chlorthal, fluorochloridone, tavron, acrolein, bentranil, tridiphane, chlorfenpropmethyl, thidiarizonaimin, phenisopham, busoxinone, methoxyphenone, saflufenacil, clacyfos, chloropon, alorac, diethamquat, etnipromid, iprymidam, ipfencarbazone, thiencarbazone-methyl, pyrimisulfan, chlorflurazole, tripropindan, sulglycapin, prosulfalin, cambendichlor, aminocyclopyrachlor, rodethanil, benoxacor, fenclorim, flurazole, fenchlorazole-ethyl, cloquintocet-mexyl, oxabetrinil, MG/91, cyometrinil, DKA-24, mefenpyr-diethyl, furilazole, fluxofenim, isoxadifen-ethyl, dichlormid, halauxifen-methyl, DOW florpyrauxifen, UBH-509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWC0535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

In the context of the present specification, if an abbreviation of a generic name of an active compound is used, it includes in each case all customary derivatives, such as esters and salts, as well as isomers, in particular optical isomers, especially one or more commercially available forms. If the generic name denotes an ester or a salt, it also includes in each case all other conventional derivatives, such as other esters and salts, free acids and neutral compounds, as well as isomers, in particular optical isomers, especially one or more commercially available forms. The chemical name given to a compound means at least one compound encompassed by the generic name, and generally the preferred compound. In the case of sulfonamides such as sulfonylurea, salts also include salts formed by the exchange of cations with hydrogen atoms in the sulfonamide group. For example, 2,4-D or 2,4-DB derivatives include but are not limited to: 2,4-D or 2,4-DB salt such as sodium salt, potassium salt, dimethylammonium salt, triethanolammonium salt, isopropylamine salt, choline, etc., and 2,4-D or 2,4-DB esters such as methyl ester, ethyl ester, butyl ester, isooctyl ester, etc.; 2-methyl-4-chloro derivatives include but are not limited to: 2-methyl-4-chloro sodium salt, -potassium salt, -dimethylammonium salt, -isopropylamine salt, etc., as well as 2-methyl-4-chloro methyl ester, -ethyl ester, -isooctyl ester, -thioethyl, etc.

For use, the formulations which are present in commercially available form are, if appropriate, diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Products in the form of dusts, granules for soil application or broadcasting and sprayable solutions are usually not further diluted with other inert substances prior to use. The application rate of the compounds of the formula I required varies with the external conditions, such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 1.0 kg a.i./ha or more of active substance, but it is preferably between 0.005 and 750 g a.i./ha, in particular between 0. 005 and 500 g a.i./ha.

SPECIFIC MODE FOR CARRYING OUT THE INVENTION

The following embodiments are used to illustrate the present invention in detail and should not be taken as any limit to the present invention. The scope of the invention would be explained through the Claims.

In view of economics and variety of a compound, we preferably synthesized several compounds, part of which are listed in the following Table A1. The structure and information of a certain compound are shown in Table A1. The compounds in Table A1 are listed for further explication of the present invention, other than any limit therefor. The subject of the present invention should not be interpreted by those skilled in the art as being limited to the following compounds.

TABLE A1 Structures and ¹H NMR data of compounds I

NO. X Y M ¹HNMR 1-1 Cl CH₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.52 (d, J = 5.5 Hz, 1H), 7.49 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 2.50 (s, 3H). 1-2 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.47 (d, J = 5.5 Hz, 1H), 7.50 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 1.54 (s, 9H). 1-3 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.45 (d, J = 5.5 Hz, 1H), 7.48 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 2.62-2.57 (m, 1H), 1.03-0.94 (m, 2H), 0.95-0.85 (m, 2H). 1-4 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.48 ((d, J = 5.5 Hz, 1H), 7.49 (d, J = 5.5 Hz, 1H), 4.25 (s, 3H), 3.05-3.01 (m, 1H), 1.99-1.95 (m, 2H), 1.73-1.70 (m, 2H), 1.60-1.45 (m, 6H). 1-5 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 11.98 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 6.03 (t, J = 7.0 Hz, 1H), 4.00 (s, 3H), 2.35-2.10 (m, 4H), 1.74 (t, J = 6.0 Hz, 2H), 1.69-1.60 (m, 2H). 1-6 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.23 (d, J = 5.0 Hz, 1H), 6.58- 6.53 (m, 1H), 4.32 (s, 3H), 3.55 (t, J = 5.5 Hz, 2H), 3.33 (dt, J = 6.5, 1.5 Hz, 2H), 3.20 (t, J = 5.5, 1.5 Hz, 2H), 1.47 (s, 9H). 1-7 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 6.12-6.09 (m, 1H), 4.31 (s, 3H), 4.20-4.15 (m, 2H), 3.79 (t, J = 5.5 Hz, 2H), 2.16-2.10 (m, 2H). 1-8 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 5.50 Hz, 1H), 7.69-7.63 (m, 2H), 7.55-7.45 (m, 3H), 3.97 (s, 3H). 1-9 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.33-7.22 (m, 3H), 7.21 (d, J = 7.5 Hz, 1H), 3.99 (s, 3H), 2.07 (s, 3H). 1-10 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.89-7.83 (m, 1H), 7.81-7.71 (m, 2H), 7.59 (t, J = 7.5 Hz, 1H), 7.32-7.21 (m, 1H), 4.33 (s, 3H), 2.47 (d, J = 1.5 Hz, 3H). 1-11 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.57 (d, J = 8.0 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H), 4.00 (s, 3H), 2.37 (s, 3H). 1-12 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.12 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.89-7.75 (m, 1H), 7.46-7.41 (m, 2H), 7.36-7.27 (m, 1H), 7.20 (d, J = 7.5 Hz, 1H), 4.01 (s, 3H), 3.33 (q, J = 7.5 Hz, 2H), 1.01 (t, J = 7.5 Hz, 3H). 1-13 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 8.0 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 3.98 (s, H), 2.62 (t, J = 8.0 Hz, 2H), 1.60-1.29 (m, 6H), 0.85 (t, J = 6.5 Hz, 3H). 1-14 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.74-7.69 (m, 2H), 7.52-7.46 (m, 2H), 4.33 (s, 3H), 2.09-1.98 (m, 2H), 1.81-1.67 (m, 4H), 1.35-1.24 (m, 2H), 1.27-1.13 (m, 6H), 0.83 (t, J = 8.0 Hz, 3H). 1-15 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 8.80 (d, J = 4.5 Hz, 1H), 7.85 (d, J = 4.5 Hz, 1H), 7.63-7.55 (m, 1H), 7.51-7.46 (m, 1H), 7.40-7.31 (m, 2H), 3.99 (s, 3H). 1-16 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.87-7.79 (m, 1H), 7.72 (d, J = 5.0 Hz, 1H), 7.69-7.63 (m, 1H), 7.48-7.46 (m, 1H), 7.32-7.20 (m, 1H), 4.33 (s, 3H). 1-17 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.79-7.69 (m, 3H), 7.39-7.26 (m, 2H), 3.99 (s, 3H) 1-18 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 7.85 (dd, J = 7.5, 2.5 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.52-7.43 (m, 2H), 7.41-7.37 (m, 1H), 4.26 (s, 3H). 1-19 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.02 (t, J = 2.0 Hz, 1H), 7.89-7.71 (m 2H), 7.68 (d, J = 5.0 Hz, 1H), 7.45 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-20 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 8.0 Hz, 2H), 7.58 (d, J = 8.0 Hz, 2H), 4.00 (s, 3H). 1-21 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.56 (d, J = 5.5 Hz, 1H), 7.96 (t, J = 2.5 Hz, 1H), 7.88-7.86 (m, 1H), 7.61 (d, J = 5.5 Hz, 1H), 7.55-7.52 (m, 1H), 7.45 (t, J = 7.5 Hz, 1H), 4.25 (s, 3H). 1-22 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.72 (d, J = 8.0 Hz, 1H), 7.66-7.60 (m, 2H), 7.56-7.45 (m, 1H), 3.99 (s, 3H). 1-23 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.56 (d, J = 5.5 Hz, 1H), 8.06 (dd, J = 7.5, 2.0 Hz, 1H), 7.61 (d, J = 5.5 Hz, 1H), 7.39-7.36 (m, 1H), 7.35-7.29 (m, 2H), 4.73 (s, 2H), 4.25 (s, 3H). 1-24 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 7.96-7.90 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.3-7.26 (m, 2H), 4.40 (s, 2H), 4.25 (s, 3H). 1-25 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.57 (d, J = 5.5 Hz, 1H), 7.89-7.82 (m, 2H), 7.72-7.66 (m, 2H), 7.50 (d, J = 5.5 Hz, 1H), 4.26 (s, 3H). 1-26 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.01 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.06-7.94 (m, 2H), 7.88 (d, J = 8.0 Hz, 1H), 7.84 (s, 1H), 7.80-7.76 (m, 1H), 4.00 (s, 3H). 1-27 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.98-7.79 (m, 5H), 4.07 (s, 3H). 1-28 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.50-7.42 (m, 1H), 7.26-7.19 (m, 1H), 7.14 (d, J = 8.5 Hz, 1H), 7.06 (t, J = 7.5 Hz, 1H), 3.98 (s, 3H), 3.74 (s, 3H). 1-29 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.68-7.57 (m, 1H), 7.33 (t, J = 7.5 Hz, 1H), 7.23 (t, J = 2.0 Hz, 1H), 6.89-6.81 (m, 1H), 4.33 (s, 3H), 3.80 (s, 3H). 1-30 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.02 (s, 1H), 8.73 (d, J = 4.5 Hz, 1H), 7.69 (d, J = 4.5 Hz, 1H), 7.66 (d, J = 8.5 Hz, 2H), 6.88 (d, J = 8.5 Hz, 2H) 3.99 (s, 3H), 3.81 (s, 3H) 1-31 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.13 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.85 (s, 1H), 7.70- 7.65 (m, 1H), 7.58-7.44 (m, 3H), 3.98 (s, 3H). 1-32 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.16 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.77-7.71 (m, 2H), 7.64 (d, J = 8.0 Hz, 1H), 4.11 (s, 3H). 1-33 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.78 (d, J = 4.5 Hz, 1H), 7.82-7.76 (m, 3H), 7.61- 7.35 (m, 2H), 4.00 (s, 3H). 1-34 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 9.74 (s, 1H), 8.54 (d, J = 5.5 Hz, 1H), 8.04 (dd, J = 7.5, 2.0 Hz, 1H), 7.49 (d, J = 5.5 Hz, 1H), 7.32-7.21 (m, 2H), 7.01 (dd, J = 7.5, 2.0 Hz, 1H), 4.25 (s, 3H). 1-35 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.63 (s, 1H), 8.71 (d, J = 4.5 Hz, 1H), 7.74-7.64 (m, 3H), 6.79-6.73 (m, 2H), 4.33 (s, 3H). 1-36 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 7.5 Hz, 1H), 7.52 (d, J = 7.5 Hz, 1H), 7.48-7.35 (m, 2H), 5.28 (s, 1H), 4.56 (s, 2H), 3.98 (s, 3H). 1-37 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.71 (d, J = 4.5 Hz, 1H), 7.88-7.82 (m, 2H), 7.70 (d, J = 4.5 Hz, 1H), 6.58-6.52 (m, 2H), 6.27 (s, 2H), 4.33 (s, 3H). 1-38 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.10 (dd, J = 6.5, 2.5 Hz, 1H), 7.97 (dd, J = 7.0, 2.5 Hz, 1H), 7.66-7.62 (m, 2H), 7.22 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-39 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 13.56 (s, 1H), 12.06 (s, 1H), 8.57 (d, J = 5.5 Hz, 1H), 8.07- 8.01 (m, 1H), 7.99-7.93 (m, 2H), 7.51 (d, J = 5.5 Hz, 1H), 4.26 (s, 3H). 1-40 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 8.0 Hz, 2H), 7.82 (d, J = 8.0 Hz, 2H), 7.32 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H), 3.88 (s, 3H). 1-41 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 8.03 (d, J = 8.0 Hz, 2H), 7.78 (d, J = 8.0 Hz, 2H), 7.35 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H), 1.56 (s, 9H). 1-42 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.81 (dd, J =7.5, 2.0 Hz, 1H), 7.45-7.34 (m, 2H), 7.23-7.18 (m, 1H), 7.10 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 2.35 (s, 3H). 1-43 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.57 (d, J = 5.5 Hz, 1H), 7.97-7.91 (m, 2H), 7.54-7.47 (m, 3H), 4.26 (s, 3H), 3.33 (hept, J = 6.5 Hz, 1H), 1.31 (d, J = 6.5 Hz, 6H). 1-44 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 8.39 (t, J = 2.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.63 (t, J = 7.5 Hz, 1H), 7.28 (d, J = 4.5 Hz, 1H), 4.32 (s, 3H), 3.25 (s, 3H). 1-45 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.01 (d, J = 8.0 Hz, 2H), 7.93 (d, J = 8.0 Hz, 2H), 7.86 (d, J = 5.0 Hz, 1H), 3.98 (s, 3H), 3.18 (s, 3H). 1-46 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 7.98 (d, J = 8.0 Hz, 2H), 7.91 (d, J = 8.0 Hz, 2H), 7.45 (d, J = 5.0 Hz, 1H), 4.03 (s, 3H), 3.73-3.64 (m, 4H), 2.95 (t, J = 4.5 Hz, 4H). 1-47 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 10.14 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.73- 7.67 (m, 3H), 7.66-7.61 (m, 2H), 3.98 (s, 3H), 2.06 (s, 3H). 1-48 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 11.36 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.86- 7.80 (m, 2H), 7.77-7.70 (m, 2H), 7.42 (t, J = 7.0 Hz, 1H), 6.48 (dd, J = 16.5, 10.0 Hz, 1H), 6.29-6.20 (m, 1H), 5.78 (dd, J = 16.5, 10.0 Hz, 1H), 4.33 (s, 3H). 1-49 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.12 (s, 1H), 7.99-7.90 (m, 2H), 7.84 (d, J = 5.0 Hz, 1H), 7.74 (t, J = 7.5 Hz, 1H), 3.99 (s, 3H). 1-50 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.00 (d, J = 8.0 Hz, 2H), 7.86 (d, J = 8.0 Hz, 2H), 7.46 (t, J = 5.0 Hz, 1H), 4.00 (s, 3H). 1-51 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.94 (d, J = 4.5 Hz, 1H), 7.70-7.64 (m, 2H), 7.35 (d, J = 4.5 Hz, 1H), 7.06-6.99 (m, 2H), 5.33 (t, J = 6.5 Hz, 1H), 4.33 (s, 3H), 3.83-3.81 (m, 1H), 3.52-3.49 (m, 1H), 2.11-1.99 (m, 1H), 1.89-1.77 (m, 2H), 1.61-1.40 (m, 3H). 1-52 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.00 (dd, J = 7.5, 2.0 Hz, 1H), 7.68-7.64 (m, 3H), 7.63-7.53 (m, 3H), 7.49-7.41 (m, 2H), 7.40-7.35 (m, 1H), 4.25 (s, 3H). 1-53 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.79 (dd, J = 5.0, 2.5 Hz, 1H), 7.92-7.67 (m, 7H), 7.51-7.47 (m, 2H), 7.42-7.34 (m, 1H), 4.00 (s, 3H). 1-54 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.14-8.08 (m, 2H), 7.90-7.81 (m, 3H), 7.65-7.59 (m, 2H), 7.40- 7.35 (m, 2H), 4.33 (s, 3H), 2.77-2.67 (m, 2H), 1.19 (t, J = 8.0 Hz, 3H). 1-55 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 7.5 Hz, 1H), 7.46 (td, J = 7.5, 2.0 Hz, 1H), 7.38 (td, J = 7.5, 2.0 Hz, 1H), 7.36-7.28 (m, 2H), 4.32 (s, 3H). 1-56 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.02 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.68-7.54 (m, 1H), 7.47-7.43 (m, 2H), 7.41 7.27 (m, 5H), 6.85-6.72 (m, 1H), 5.10 (s, 2H), 4.33 (s, 3H). 1-57 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.24 (dd, J = 7.5, 2.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 7.52-7.48 (m, 1H), 7.43-7.33 (m, 3H), 7.32-7.28 (m, 1H), 7.14-7.10 (m, 1H), 7.09-7.04 (m, 2H), 4.33 (s, 3H). 1-58 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.51 (d, J = 5.5 Hz, 1H), 7.59 (d, J = 5.5 Hz, 1H), 7.31-7.23 (m, 3H), 4.25 (s, 3H), 2.38 (s, 6H). 1-59 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.13-7.05 (m, 2H), 4.33 (s, 3H), 2.43 (d, J = 1.0 Hz, 3H), 2.31 (s, 3H). 1-60 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.01 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.73 (s, 1H), 7.24 (s, 2H), 7.11 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 2.33 (s, 6H). 1-61 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.74 (d, J = 5.5 Hz, 1H), 7.81-7.78 (m, 2H), 7.56 (d, J = 5.5 Hz, 1H), 7.49 (t J = 2.5 Hz, 1H), 4.26 (s, 3H), 1.31 (s, 18H). 1-62 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.50 (d, J = 5.5 Hz, 1H), 7.68-7.65 (m, 1H), 7.59 (d, J = 5.5 Hz, 1H), 7.40-7.27 (m, 2H), 4.26 (s, 3H). 1-63 Cl

¹H NMR (500 MHz, DMSO-d6) δ 11.85 (s, 1H), 8.74 (d, J = 4.5 Hz, 1H), 7.64-7.58 (m, 1H), 7.39- 7.32 (m, 1H), 7.2-7.15 (m, 1H), 7.08 (d, J = 4.5 Hz, 1H), 4.31 (s, 3H). 1-64 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 5.0 Hz, 1H), 7.57-7.52 (m, 1H), 7.44 (t, J = 10.0 Hz, 1H), 7.26 (dd, J = 8.5, 7.0 Hz, 1H), 3.99 (s, 3H). 1-65 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 7.40 (t, J = 9.0 Hz, 2H), 7.25-7.20 (m, 1H), 3.99 (s, 3H). 1-66 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.78 (d, J = 5.5 Hz, 1H), 7.86-7.70 (m, 2H), 7.66-7.49 (m, 2H), 4.00 (s, 3H),. 1-67 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 7.29-7.19 (m, 3H), 3.99 (s, 3H), 2.34 (s, 3H). 1-68 Cl

¹H NMR (500 MHz, DMSO-d6) δ 11.96 (s, 1H), 8.78 (d, J = 4.5 Hz, 1H), 7.54 (d, J = 8.5, 1H), 7.37 (dd, J = 7.5, 2.0 Hz, 1H), 7.26 (d, J = 4.5 Hz, 1H), 7.20-7.16 (m, 1H), 4.32 (s, 3H), 2.29 (s, 3H). 1-69 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.80 (s, 1H), 7.35 (t, J = 8.0 Hz, 1H), 7.17 (t, J = 10.5 Hz, 2H), 3.98 (s, 3H), 2.39 (s, 3H),. 1-70 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.51 (d, J = 5.5 Hz, 1H), 7.56 (d, J = 5.5 Hz, 1H), 7.42-7.38 (m, 1H), 7.13-7.10 (m, 1H), 6.82-6.80 (m, 1H), 4.26 (s, 3H), 3.85 (s, 3H). 1-71 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.48 (d, J = 5.5 Hz, 1H), 7.56-7.49 (m, 2H), 7.17 (t, J = 2.0 Hz, 1H), 6.80-6.75 (m, 1H), 4.26 (s, 3H), 3.80 (s, 3H). 1-72 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.84 (d, J = 4.5 Hz, 1H), 7.34-7.19 (m, 2H), 6.98-6.95 (m, 1H), 3.99 (s, 3H), 3.88 (s, 3H). 1-73 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.55 (d, J = 5.5 Hz, 1H), 7.80 (dd, J = 8.5, 7.5 Hz, 1H), 7.60-7.50 (m, 2H), 7.23-7.20 (m, 1H), 4.25 (s, 3H). 1-74 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.45-7.39 (m, 1H), 7.33-7.23 (m, 2H), 4.32 (s, 3H). 1-75 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.14 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.94-7.84 (m, 3H), 7.65-7.51 (m, 1H), 3.99 (s, 3H). 1-76 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.55 (d, J = 5.5 Hz, 1H), 8.05 (d, J = 8.5 Hz, 1H), 7.84 (d, J = 2.0 Hz, 1H), 7.74 (dd, J = 8.5, 2.0 Hz, 1H), 7.58 (d, J = 5.5 Hz, 1H), 4.26 (s, 3H). 1-77 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.19 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.49 (s, 2H), 8.42 (s, 1H), 8.02 (d, J = 5.0 Hz, 1H), 4.12 (s, 3H). 1-78 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.05-7.95 (m, 2H), 7.69 (d, J = 5.5 Hz, 1H), 7.51 (dd, J = 13.5, 2.5 Hz, 1H), 4.33 (s, 3H). 1-79 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 8.70 (d, J = 5.5 Hz, 1H), 7.96-7.89 (m, 2H), 7.76 (dd, J = 8.0, 7.0 Hz, 1H), 7.71 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-80 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.12-8.08 (m, 1H), 7.82-7.78 (m, 1H), 7.69 (d, J = 5.5 Hz, 1H), 7.32 (dt, J = 7.5, 2.5 Hz, 1H), 4.33 (s, 3H). 1-81 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.70 (d, J = 5.5 Hz, 1H), 8.06-7.95 (m, 2H), 7.89 (t, J = 2.0 Hz, 1H), 7.70-7.68 (m, 1H), 4.33 (s, 3H). 1-82 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.07 (dd, J = 7.5, 2.0 Hz, 1H), 7.77-7.73 (m, 1H), 7.70 (d, J = 5.5 Hz, 1H), 7.45 (dd, J = 11.5, 7.5 Hz, 1H), 4.33 (s, 3H). 1-83 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.70 (d, J = 5.5 Hz, 1H), 7.99-7.95 (m, 2H), 7.67 (d, J = 5.5 Hz, 1H), 7.49-7.45 (m, 1H), 4.33 (s, 3H). 1-84 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.26-8.21 (m, 1H), 8.16 (dd, J = 8.0, 2.5 Hz, 1H), 7.70 (d, J = 5.5 Hz, 1H), 7.47 (dd, J = 13.5, 7.5 Hz, 1H), 4.33 (s, 3H). 1-85 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.17-8.01 (m, 2H), 7.84 (d, J = 7.5 Hz, 1H), 7.69-7.64 (m, 1H), 4.00 (s, 3H),. 1-86 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.90-7.85 (m, 1H), 7.81 (d, J = 2.0 Hz, 1H), 7.58 (dd, J = 8.5, 2.0 Hz, 1H), 7.48 (d, J = 8.5 Hz, 1H), 3.99 (s, 3H). 1-87 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.18 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 7.0 Hz, 1H), 7.84-7.77 (m, 1H), 7.58-7.51 (m, 1H), 7.44 (d, J = 7.0 Hz, 1H), 4.02 (s, 3H). 1-88 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 2.0 Hz, 1H), 7.85-7.77 (m, 2H), 7.70-7.67 (m, 1H), 4.00 (s, 3H). 1-89 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.84 (d, J = 4.5 Hz, 1H), 7.78 (t, J = 2.0 Hz, 1H), 7.71 (d, J = 2.0 Hz, 2H), 3.99 (s, 3H). 1-90 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.84 (d, J = 4.5 Hz, 1H), 7.62 (dt, J = 9.0, 2.0 Hz, 1H), 7.57 (s, 1H), 7.52 (d, J = 9.0 Hz, 1H), 3.99 (s, 3H). 1-91 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.82 (d, J = 9.0 Hz, 1H), 7.76-7.71 (m, 2H), 7.55 (d, J = 8.5 Hz, 1H), 3.99 (s, 3H). 1-92 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.87-7.81 (m, 2H), 7.68 (d, J = 5.0 Hz, 1H), 7.29-7.22 (m, 1H), 4.33 (s, 3H). 1-93 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.73-7.66 (m, 1H), 7.54- 7.42 (m, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.18 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-94 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 5.0 Hz, 1H), 7.64 (dd, J = 9.0, 2.5 Hz, 1H), 7.51 (dd, J = 8.5, 6.0 Hz, 1H), 7.38-7.30 (m, 1H), 3.98 (s, 3H). 1-95 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.69-7.62 (m, 1H), 7.55 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 8.0, 2.0 Hz, 1H), 3.99 (s, 3H). 1-96 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 8.62 (d, J = 5.5 Hz, 1H), 7.84 (d, J = 2.0 Hz, 1H), 7.71 (d, J = 8.5 Hz, 1H), 7.62 (d, J = 5.5 Hz, 1H), 7.55 (dd, J = 8.5, 2.0 Hz, 1H), 4.26 (s, 3H). 1-97 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.54 (d, J = 5.5 Hz, 1H), 7.84-7.80 (m, 1H), 7.65- 7.56 (m, 2H), 7.28-7.24 (m, 1H), 4.26 (s, 3H). 1-98 Cl

¹H NMR (500 MHz, DMSO-d6) δ 11.99 (s, 1H), 8.75 (d, J = 4.5 Hz, 1H), 8.14 (d, J = 2.0 Hz, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 7.5 Hz, 1H), 7.09 (d, J = 4.5 Hz, 1H), 4.32 (s, 3H), 3.94 (s, 3H). 1-99 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 11.26 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.38 (d, J = 2.0 Hz, 1H), 8.02 (dd, J = 7.5, 2.0 Hz, 1H), 7.68 (d, J = 5.0 Hz, 1H), 7.09 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H), 3.90 (s, 3H). 1-100 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 13.19 (s, 1H), 12.01 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.70 (s, 1H), 8.66 (s, 1H), 7.88 (s, 1H), 7.63 (d, J = 4.5 Hz, 1H), 4.00 (s, 3H). 1-101 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.76 (d, J = 4.5 Hz, 1H), 7.81 (d, J = 7.5 Hz, 1H), 7.66-7.62 (m, 1H), 7.39 (dd, J = 7.5, 2.0 Hz, 1H), 7.24 (d, J = 4.5 Hz, 1H), 4.33 (s, 3H). 1-102 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 8.75 (d, J = 4.5 Hz, 1H), 7.81 (d, J = 4.5 Hz, 1H), 7.36-7.30 (m, 1H), 7.17 (d, J = 2.5 Hz, 1H), 7.07-7.01 (m, 1H), 3.98 (s, 3H), 3.83 (s, 3H). 1-103 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.20 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 9.0 Hz, 1H), 7.23-7.15 (m, 1H), 7.05 (d, J = 3.0 Hz, 1H), 4.08 (s, 3H), 3.86 (s, 3H). 1-104 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.16 (d, J = 8.5 Hz, 1H), 6.92 (d, J = 2.5 Hz, 1H), 6.88 (d, J = 8.5, 2.5 Hz, 1H), 4.01 (s, 3H), 3.81 (s, 3H), 2.09 (s, 3H). 1-105 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.14 (d, J = 8.5 Hz, 1H), 6.70-6.59 (m, 2H), 3.97 (s, 3H), 3.81 (s, 3H), 3.73 (s, 3H). 1-106 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.81 (d, J = 5.0 Hz, 1H), 7.41-7.29 (m, 6H), 7.03-6.95 (m, 2H), 5.18 (s, 2H), 3.98 (s, 3H). 1-107 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 7.84-7.75 (m, 2H), 7.70 (dd, J = 7.5, 2.0 Hz, 1H), 7.50-7.44 (m, 2H), 7.42 (d, J = 7.5 Hz, 1H), 7.41-7.34 (m, 2H), 7.32-7.28 (m, 1H), 4.33 (s, 3H). 1-108 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.13 (d, J = 2.0 Hz, 2H), 7.96 (t, J = 2.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.73 (dd, J = 7.5, 2.0 Hz, 4H), 7.49 (t, J = 7.5 Hz, 4H), 7.43-7.35 (m, 2H), 4.33 (s, 3H). 1-109 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.79 (d, J = 4.5 Hz, 1H), 7.67-7.60 (m, 2H), 7.55-7.42 (m, 1H), 3.99 (s, 3H). 1-110 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 7.48 (dd, J = 7.5, 1.5 Hz, 1H), 7.26 (t, J = 7.5 Hz, 1H), 4.00 (s, 3H), 3.92 (s, 3H). 1-111 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.19 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.04-7.98 (m, 2H), 7.87 (d, J = 5.0 Hz, 1H), 7.64 (t, J = 7.5 Hz, 1H), 7.53-7.42 (m, 3H), 7.36 (d, J = 8.5 Hz, 1H), 3.98 (s, 3H). 1-112 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.13-8.06 (m, 2H), 7.99 (d, J = 7.5 Hz, 1H), 7.82 (d, J = 5.0 Hz, 1H), 7.79- 7.73 (m, 2H), 7.62-7.56 (m, 2H), 4.01 (s, 3H). 1-113 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.91 (d, J = 5.5 Hz, 1H), 8.33 (dd, J = 7.5, 1.5 Hz, 1H), 8.22 (dd, J = 7.5, 1.5 Hz, 1H), 8.03-7.99 (m, 1H), 7.84 (d, J = 5.5 Hz, 1H), 7.53-7.50 (m, 1H), 7.37 (dd, J = 7.5, 8.0 Hz, 1H), 6.63-6.60 (m, 1H), 4.33 (s, 3H). 1-114 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 9.28 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.60 (d, J = 7.5 Hz, 1H), 8.18-8.10 (m, 2H), 7.88-7.78 (m, 3H), 4.33 (s, 3H). 1-115 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 8.94-8.86 (m, 2H), 8.78 (d, J = 5.5 Hz, 1H), 8.38 (s, 1H), 8.05-7.95 (m, 2H), 7.86 (d, J = 5.0 Hz, 1H), 7.74-7.61 (m, 4H), 4.33 (s, 3H). 1-116 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.30 (d d, J = 7.5, 1.5 Hz, 1H), 8.22 (d, J = 7.5 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.64-7.58 (m, 1H), 7.59-7.49 (m, 2H), 7.43 (t, J = 7.5 Hz, 1H), 4.01 (s, 3H). 1-117 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.01 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.13 (d, J = 1.5 Hz, 1H), 8.09-8.01 (m, 2H), 7.95 (dd, J = 7.5, 1.5 Hz, 1H), 7.81 (d, J = 5.0 Hz, 1H), 7.54 (dd, J = 7.5, 1.5 Hz, 1H), 7.48-7.41 (m, 1H), 7.37-7.32 (m, 1H), 4.33 (s, 3H). 1-118 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.51-8.38 (m, 3H), 7.98 (d, J = 5.0 Hz, 1H), 7.74 (s, 2H), 7.67-7.64 (m, 1H), 7.52 (s, 1H), 3.88 (s, 3H). 1-119 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.63 (d, J = 5.5 Hz, 1H), 8.22 (dd, J = 8.0, 2.0 Hz, 1H), 7.82 (t, J = 8.0 Hz, 1H), 7.69 (d, J = 5.5 Hz, 1H), 7.41-7.38 (m, 1H), 4.25 (s, 3H). 1-120 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.89 (d, J = 7.5, 1H), 8.75 (d, J = 5.5 Hz, 1H), 7.92 (t, J = 7.5 Hz, 1H), 7.82 (d, J = 5.5 Hz, 1H), 7.65 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-121 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 9.11 (s, 1H), 8.75 (d, J = 5.5 Hz, 1H), 8.54 (d, J = 8.0 Hz, 1H), 8.19 (d, J = 8.0 Hz, 1H), 7.83 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-122 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.80 (d, J = 5.5 Hz, 1H), 8.71 (d, J = 5.5 Hz, 1H), 8.56 (s, 1H), 7.78 (d, J = 5.5 Hz, 1H), 7.53 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-123 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.76 (d, J = 5.5 Hz, 1H), 8.68 (dd, J = 8.0, 2.5 Hz, 1H), 8.22 (dd, J = 12.5, 2.5 Hz, 1H), 7.80 (d, J = 5.5 Hz, 1H), 7.62-7.58 (m, 1H), 4.33 (s, 3H). 1-124 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.86 (d, J = 2.5 Hz, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.69-8.68 (m, 1H), 8.11 (d, J = 8.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 7.57-7.55 (m, 1H), 4.00 (s, 3H). 1-125 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.56-8.49 (m, 1H), 8.48 (d, J = 5.0 Hz, 1H), 8.35 (s, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.36 (d, J = 5.0 Hz, 1H), 3.68 (s, 3H), 2.10 (s, 3H). 1-126 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 8.65 (s, 1H), 8.52 (s, 1H), 7.90 (s, 1H), 7.81 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 2.38 (s, 3H). 1-127 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.27 (dd, J = 5.5, 1.5 Hz, 1H), 8.18-8.16 (m, 1H), 7.78-7.75 (m, 1H), 7.72 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-128 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.77-8.71 (m, 2H), 8.40-8.36 (m, 2H), 7.88 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-129 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.80 (d, J = 4.5 Hz, 1H), 8.72 (d, J = 2.5 Hz, 1H), 8.20-8.18 (m, 1H), 7.82 (d, J = 4.5 Hz, 1H), 7.69 (d, J = 8.0 Hz, 1H), 3.97 (s, 3H). 1-130 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.35 (dd, J = 5.0, 2.0 Hz, 1H), 8.07-8.02 (m, 1H), 7.92-7.85 (m, 2H), 4.33 (s, 3H). 1-131 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.81 (d, J = 1.5 Hz, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.02 (dd, J = 8.0, 1.5 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H). 1-132 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.83 (d, J = 5.5 Hz, 1H), 8.75 (d, J = 7.5 Hz, 1H), 8.18 (dd, J = 7.5, 7.5 Hz, 1H), 7.98 (d, J = 5.5 Hz, 1H), 7.18 (dd, J = 12.5, 7.5 Hz, 1H), 4.33 (s, 3H). 1-133 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 9.25 (s, 1H), 9.08 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.68 (s, 1H), 8.00 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-134 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.98 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.24 (d, J = 8.0 Hz, 1H), 7.99 (d, J = 5.5 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H). 1-135 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.38-8.33 (m, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.16-7.11 (m, 1H), 4.33 (s, 3H). 1-136 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.14 (s, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.26 (d, J = 6.0 Hz, 1H), 3.99 (s, 3H), 2.17 (s, 3H). 1-137 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.02 (s, 1H), 8.85 (d, J = 4.5 Hz, 1H), 8.28 (dd, J = 11.0, 8.0 Hz, 1H), 7.52 (d, J = 4.5 Hz, 1H), 6.88 (dd, J = 8.0, 7.0 Hz, 1H), 4.32 (s, 3H), 2.79 (s, 3H). 1-138 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.88-8.82 (m, 2H), 7.54-7.47 (m, 2H), 4.32 (s, 3H), 2.37 (s, 3H). 1-139 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.84 (d, J = 4.5 Hz, 1H), 8.36 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 8.0 Hz, 1H), 7.33 (d, J = 4.5 Hz, 1H), 4.32 (s, 3H). 1-140 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.18 (dd, J = 8.0, 6.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H). 1-141 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.86 (d, J = 4.5 Hz, 1H), 8.69 (dd, J = 5.0, 1.5 Hz, 1H), 8.26 (dd, J = 8.0, 1.5 Hz, 1H), 7.67 (dd, J = 8.0, 5.0 Hz, 1H), 7.36 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-142 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 9.07 (d, J = 2.0 Hz, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.46-8.38 (m, 1H), 8.09 (d, J = 8.0 Hz, 1H), 7.91 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H). 1-143 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.19 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.63 (d, J = 2.5 Hz, 1H), 8.21-8.08 (m, 1H), 7.88 (d J = 5.0 Hz, 1H), 7.08 (d, J = 8.5 Hz, 1H), 4.11 (s, 3H), 4.03 (s, 3H). 1-144 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.59 (d, J = 1.5 Hz, 1H), 8.03 (dd, J = 8.0, 1.5 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.09 (d, J = 8.0 Hz, 1H), 4.33 (q, J = 8.0 Hz, 2H), 4.33 (s, 3H), 1.28 (t, J = 8.0 Hz, 3H). 1-145 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.84 (d, J = 4.5 Hz, 1H), 8.38 (d, J = 1.5 Hz, 1H), 8.04-7.95 (m, 2H), 7.46 (t, J = 1.5 Hz, 1H), 6.18 (s, 2H), 4.33 (s, 3H). 1-146 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.14 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.53 (d, J = 2.5 Hz, 1H), 8.01 (dd, J = 9.0, 2.5 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.03 (d, J = 9.0 Hz, 1H), 4.03 (s, 3H), 3.73 (t, J = 5.0 Hz, 4H), 3.60 (t, J = 5.0 Hz, 4H). 1-147 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.66 (d, J = 5.0 Hz, 2H), 8.04 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-148 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.85 (d, J = 5.5 Hz, 1H), 8.78 (d, J = 5.5 Hz, 1H), 8.53 (s, 1H), 8.29 (d, J = 5.5 Hz, 1H), 8.00 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-149 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.27 (d, J = 5.0 Hz, 1H), 8.06-7.97 (m, 2H), 7.84 (dd, J = 5.0, 1.0 Hz, 1H), 4.33 (s, 3H). 1-150 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 8.0 Hz, 1H), 8.33 (d, J = 4.5 Hz, 1H), 7.73 (dd, J = 8.0, 4.5 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-151 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.42-8.34 (m, 2H), 8.06-7.96 (m, 2H), 4.33 (s, 3H). 1-152 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.40 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-153 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.49 (s, 2H), 8.11 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-154 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.94 (dd, J = 7.5, 7.5 Hz, 1H), 8.89 (d, J = 5.5 Hz, 1H), 8.01 (d, J = 5.5 Hz, 1H), 7.68 (dd, J = 12.0, 7.5 Hz, 1H), 4.33 (s, 3H). 1-155 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.94 (d, J = 7.5 Hz, 1H), 8.89 (d, J = 5.5 Hz, 1H), 8.34 (d, J = 7.5 Hz, 1H), 8.01 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-156 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 9.40 (s, 2H), 9.35 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-157 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 9.27 (s, 2H), 8.79 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-158 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 9.45 (d, J = 7.5 Hz, 2H), 8.89 (d, J = 5.5 Hz, 1H), 7.98 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-159 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 9.01 (s, 2H), 8.90 (d, J = 5.5 Hz, 1H), 7.96 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-160 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.63 (s, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.11 (s, 2H), 4.00 (s, 3H). 1-161 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 9.50 (s, 2H), 8.89 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.85 (s, 3H). 1-162 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.34 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.74 (s, 1H), 7.31 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 3.98 (s, 3H), 3.84 (s, 3H). 1-163 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 9.25 (s, 2H), 8.86 (d, J = 5.5 Hz, 1H), 8.00 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-164 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.88 (d, J = 5.5 Hz, 1H), 8.84 (d, J = 12.5, 2.5 Hz, 2H), 7.99 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-165 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 9.10 (d, J = 5.0 Hz, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.02 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-166 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H), 7.50 (d, J = 12.5 Hz, 2H), 4.33 (s, 3H). 1-167 Cl

1H NMR (500 MHz, DMSO-d6) δ 13.15 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.22 (s, 2H), 7.16 (d, J = 5.0 Hz, 1H), 3.70 (s, 3H). 1-168 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.63 (s, 1H), 8.25 (s, 1H), 7.68 (d, J = 5.0 Hz, 1H), 4.12 (s, 3H), 4.03 (s, 3H). 1-169 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.01 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.20 (s, 1H), 7.59 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 3.82 (s, 3H), 2.28 (s, 3H). 1-170 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.99 (d, J = 5.0 Hz, 1H), 7.67 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.94 (s, 3H), 2.34 (s, 3H). 1-171 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 13.53 (s, 1H), 12.03 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H), 7.40 (s, 1H), 4.33 (s, 3H), 2.31 (s, 3H). 1-172 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.02 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.53 (s, 1H), 8.15 (s, 1H), 7.56 (d, J = 5.0 Hz, 1H), 4.21-4.15 (m, 2H), 4.00 (s, 3H), 1.40 (t, J = 7.0 Hz, 3H). 1-173 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 1.5 Hz, 1H), 7.47 (d, J = 5.0 Hz, 1H), 6.91 (d, J = 1.5 Hz, 1H), 4.33 (s, 3H), 4.20 (t, J = 8.0 Hz, 2H), 2.00 (m, 2H), 0.95 (t, J = 8.0 Hz, 3H). 1-174 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.91 (d, J = 5.5 Hz, 1H), 7.95 (t, J = 65.0 Hz, 1H), 7.71 (d, J = 5.5 Hz, 1H), 7.67 (s, 1H), 7.06 (s, 1H)), 4.33 (s, 3H). 1-175 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.13 (s, 1H), 8.95-8.69 (m, 2H), 8.30 (d, J = 5.5 Hz, 1H), 7.68 (s, 1H), 7.42-7.29 (m, 5H), 5.53 (s, 2H), 4.11 (s, 3H). 1-176 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.66-8.59 (m, 2H), 8.22 (s, 1H), 7.60 (d, J = 5.5 Hz, 1H), 5.65-5.60 (m, 1H), 4.00 (s, 3H), 3.51- 3.41 (m, 2H), 1.63 (d, J = 6.0 Hz, 3H), 1.06-0.97 (m, 3H). 1-177 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 13.56 (s, 1H), 12.13 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.30 (d, J = 2.5 Hz, 1H), 7.89 (d, J = 2.5 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 4.00 (s, 3H). 1-178 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 2.5 Hz, 1H), 7.61-7.44 (m, 1H), 6.67 (d, J = 5.0 Hz, 1H), 3.99 (s, 3H), 3.83 (s, 3H). 1-179 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.98 (d, J = 4.5 Hz, 1H), 7.51 (d, J = 4.5 Hz, 1H), 6.55 (s, 1H), 4.33 (s, 3H), 4.00 (s, 3H), 2.35 (s, 3H). 1-180 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.51 (d, J = 5.0 Hz, 1H), 6.68 (s, 1H), 4.33 (s, 3H), 4.02 (s, 3H). 1-181 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.96-7.73 (t, J = 6.5 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 7.64 (d, J = 2.5 Hz, 1H), 6.73 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-182 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.10 (d, J = 5.0 Hz, 1H), 7.61 (d, J = 2.5 Hz, 1H), 6.68 (d, J = 2.5 Hz, 1H), 6.12 (t, J = 6.5 Hz, 1H), 4.33 (s, 3H), 3.90-3.77 (m, 2H), 2.47-2.36 (m, 1H), 2.08- 1.95 (m, 2H), 1.81-1.69 (m, 1H), 1.59-1.55 (m, 2H). 1-183 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.16 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.66 (s, 1H), 7.98-7.88 (m, 1H), 7.78 (d, J = 2.0 Hz, 1H), 7.25 (d, J = 2.0 Hz, 1H), 4.20 (s, 3H). 1-184 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.10-8.04 (m, 2H), 7.25 (d, J = 2.5 Hz, 1H), 6.98 (t, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-185 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 9.25 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 5.0 Hz, 1H), 7.29 (d, J = 2.5 Hz, 1H), 7.22 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-186 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.20 (dd, J = 3.0, 1.5 Hz, 1H), 7.74-7.58 (m, 3H), 4.01 (s, 3H). 1-187 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 2.5 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 6.92 (d, J = 2.5 Hz, 1H), 4.00 (s, 3H), 2.38 (s, 3H). 1-188 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.97 (s, 1H), 7.67 (d, J = 5.0 Hz, 1H), 7.42 (s, 1H), 4.03 (s, 3H), 2.29 (s, 3H). 1-189 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.99 (d, J = 5.0 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 7.08 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-190 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 9.87 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 8.10 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 2.5 Hz, 1H), 7.81 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-191 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.11 (d, J = 2.5 Hz, 1H), 7.82 (d, J = 2.5 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.50 (s, 3H). 1-192 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.59-7.51 (m, 2H), 4.33 (s, 3H), 4.26 (s, 1H). 1-193 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.91 (d, J = 5.5 Hz, 1H), 8.45 (s, 1H), 8.09 (s, 1H), 7.91 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-194 CH₃

¹H NMR (500 MHz, DMSO-d6) δ 12.31 (s, 1H), 8.69 (d, J = 4.5 Hz, 1H), 7.60-7.52 (m, 2H), 7.14-7.03 (m, 3H), 4.33 (s, 3H), 2.35 (s, 3H). 1-195 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.44 (dd, J = 5.0, 1.5 Hz, 1H), 8.08-8.01 (m, 2H), 7.83 (dd, J = 7.5, 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H). 1-196 Br

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.80 (d, J = 5.5 Hz, 1H), 7.96 (dd, J = 7.5, 7.0 Hz, 2H), 7.72 (d, J = 5.5 Hz, 1H), 7.33 (dd, J = 12.0, 7.0 Hz, 2H), 4.33 (s, 3H). 1-197

¹H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.54-7.45 (m, 2H), 7.11-7.03 (m, 2H), 7.00 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 3.16-3.11 (m, 1H), 1.25 (d, J = 6.5 Hz, 6H). 1-198 CF₃

¹H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.87 (d, J = 4.5 Hz, 1H), 7.64-7.56 (m, 2H), 7.13 (d, J = 4.5 Hz, 1H), 7.11-7.03 (m, 2H), 4.35 (s, 3H). 1-199

¹H NMR (500 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.61-7.53 (m, 4H), 7.42 (t, J = 7.5 Hz, 1H), 7.40 (d, J = 7.5 Hz, 1H), 7.37-7.29 (m, 2H), 7.11-7.03 (m, 2H), 4.29 (s, 3H). 1-200

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.71-7.63 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H) 4.34 (s, 3H), 3.79 (s, 3H). 1-201

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.71-7.64 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.34-4.06 (m, 2H), 4.34 (s, 3H), 1.61 (t, J = 8.0 Hz, 3H). 1-202

¹H NMR (500 MHz, DMSO-d₆) δ 11.93 (s, 1H), 8.67 (d, J = 4.5 Hz, 1H), 7.72-7.64 (m, 2H), 7.42 (d, J = 4.5 Hz, 1H), 7.11-7.03 (m, 2H), 4.46-4.39 (m, 2H), 4.34 (s, 3H). 1-203

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.60 (d, J = 5.5 Hz, 1H), 8.02 (dd, J = 7.5, 7.5 Hz, 2H), 7.60 (d, J = 5.5 Hz, 1H), 7.32 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 2.21 (s, 3H). 1-204

¹H NMR (500 MHz, DMSO-d6) δ 11.82 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.64-7.56 (m, 2H), 7.24 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.33 (s, 3H), 2.97-2.89 (m, 2H), 1.28 (t, J = 8.0 Hz, 3H). 1-205

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.87 (d, J = 5.5 Hz, 1H), 7.98 (dd, J = 7.5, 7.5 Hz, 2H), 7.65 (d, J = 5.5 Hz, 1H), 7.33 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 2.61 (s, 3H). 1-206

¹H NMR (500 MHz, DMSO-6) δ 12.02 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 7.66-7.59 (m, 2H), 7.28 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.30 (s, 3H), 3.25-3.16 (m, 2H), 1.35 (t, J = 8.0 Hz, 3H). 1-207

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 9.02 (d, J = 5.5 Hz, 1H), 8.12 (dd, J = 7.5, 7.5 Hz, 2H), 7.78 (d, J = 5.5 Hz, 1H), 7.31 (dd, J = 12.0, 7.5 Hz, 2H), 4.33 (s, 3H), 2.94 (s, 3H). 1-208

¹H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.48 (d, J = 4.5 Hz, 1H), 7.57-7.47 (m, 3H), 7.11-7.03 (m, 2H), 4.33 (s, 3H), 2.89 (s, 6H). 1-209

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.49 (d, J = 5.5 Hz, 1H), 8.05 (dd, J = 7.5, 7.5 Hz, 2H), 7.89 (d, J = 5.5 Hz, 1H), 7.27 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 2.35 (s, 6H). 1-210 Et

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.58 (d, J = 5.5 Hz, 1H), 7.96-7.88 (m, 2H), 7.40 (d, J = 5.5 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 2.70 (q, J = 8.0 Hz, 2H), 1.07 (t, J = 8.0 Hz, 3H). 1-211

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.54 (d, J = 5.5 Hz, 1H), 8.06-7.98 (m, 2H), 7.53 (d, J = 5.5 Hz, 1H), 7.35-7.27 (m, 2H), 5.02 (s, 2H), 4.33 (s, 3H). 1-212 NO₂

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 8.78 (d, J = 5.5 Hz, 1H), 7.92 (dd, J = 7.5, 7.0 Hz, 2H), 7.79 (d, J = 5.5 Hz, 1H), 7.27 (dd, J = 11.0, 7.5 Hz, 2H), 4.33 (s, 3H). 1-213 CN

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.80 (d, J = 5.5 Hz, 1H), 7.98 (dd, J = 7.5, 7.0 Hz, 2H), 7.72 (d, J = 5.5 Hz, 1H), 7.31 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H). 1-214

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 4.33 (s, 3H), 3.28 (s, 3H). 1-215

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.97-7.90 (m, 2H), 7.79 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.64 (q, J = 7.0 Hz, 1H), 4.33 (s, 3H), 3.23 (s, 3H), 1.36 (d, J = 7.0 Hz, 3H). 1-216

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.97-7.90 (m, 2H), 7.79 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.36 (t, J = 8.0 Hz, 1H), 4.33 (s, 3H), 3.22 (s, 3H), 1.77-1.62 (m, 2H), 0.85 (t, J = 8.0 Hz, 3H). 1-217

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.61 (d, J = 5.0 Hz, 1H), 7.93-7.85 (m, 2H), 7.40 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 3.48 (t, J = 7.5 Hz, 2H), 3.23 (s, 3H), 2.75 (t, J = 7.5 Hz, 2H). 1-218

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.69 (d, J = 5.5 Hz, 1H), 8.0.1 (dd, J = 7.5, 7.0 Hz, 2H), 7.47 (d, J = 5.5 Hz, 1H), 7.27 (dd, J = 12.0, 7.5 Hz, 2H), 6.59 (dd, J = 16.5, 10.5 Hz, 1H), 5.55 (dd, J = 13.5, 10.5 Hz, 1H), 5.36 (dd, J = 16.5, 13.5 Hz, 1H), 4.33 (s, 3H). 1-219

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.45 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 5.69-5.65 (m, 1H), 5.06-4.92 (m, 2H), 4.33 (s, 3H), 3.33-3.30 (m, 2H). 1-220

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.72 (d, J = 5.5 Hz, 1H), 8.07 (dd, J = 7.5, 7.5 Hz, 2H), 7.57 (d, J = 5.5 Hz, 1H), 7.35 (dd, J = 11.5, 7.5 Hz, 2H), 4.33 (s, 3H), 4.31 (s, 1H). 1-221

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 2.25 (p, J = 7.0 Hz, 1H), 0.91- 0.81 (m, 2H), 0.70-0.66 (m, 2H). 1-222

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.00-7.92 (m, 2H), 7.35-7.27 (m, 3H), 4.90 (s, 1H), 4.33 (s, 3H). 1-223

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 9.02 (d, J = 5.5 Hz, 1H), 7.99 (dd, J = 7.5, 7.5 Hz, 2H), 7.78 (d, J = 5.5 Hz, 1H), 7.55 (dd, J = 7.5, 7.0 Hz, 2H), 7.35 (dd, J = 11.5, 7.5 Hz, 2H), 7.23 (dd, J = 11.0, 7.5 Hz, 2H), 4.33 (s, 3H). 1-224 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 9.17 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 6.50 (d, J = 2.5 Hz, 1H), 6.10 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H), 3.63 (s, 3H). 1-225 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.82 (d, J = 5.0 Hz, 1H), 7.02 (s, 1H), 6.91 (d, J = 2.0 Hz, 1H), 6.61 (d, J = 2.0 Hz, 1H), 4.37 (q, J = 9.0 Hz, 2H), 4.33 (s, 3H). 1-226 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.09 (s, 1H), 7.93 (d, J = 5.0 Hz, 1H), 7.70 (s, 1H), 4.33 (s, 3H). 1-227 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.13 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.86 (d, J = 2.5 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.36 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-228 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 9.19 (s, 1H), 8.92 (d, J = 5.5 Hz, 1H), 8.03 (s, 1H), 7.94 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-229 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 9.19 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.12 (s, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-230 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.93 (d, J = 5.5 Hz, 1H), 8.04 (d, J = 2.5 Hz, 1H), 7.96 (d, J = 5.5 Hz, 1H), 7.50 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-231 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.72 (s, 1H), 7.98 (s, 1H), 7.92 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-232 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 2.5 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.33 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-233 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.90 (d, J = 5.5 Hz, 1H), 7.95 (d, J = 2.5 Hz, 1H), 7.39 (d, J = 5.5 Hz, 1H), 7.05 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H), 3.92 (s, 3H). 1-234 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 5.0 Hz, 1H), 7.73 (s, 1H), 7.67 (s, 1H), 4.33 (s, 3H), 3.79 (s, 3H). 1-235 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 7.61 (s, 1H), 6.70 (t, J = 65 Hz, 1H), 4.33 (s, 3H), 3.54 (s, 3H). 1-236 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.18 (s, 1H), 7.75 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-237 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.14 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.45 (s, 1H), 7.77 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-238 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 7.69 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-239 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.79 (d, J = 5.0 Hz, 1H), 7.74 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-240 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.27 (s, 1H), 7.86 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-241 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.18 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.35-4.25 (m, 5H), 2.51 (s, 3H), 1.39 (t, J = 8.0 Hz, 3H). 1-242 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 7.82 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-243 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.19 (s, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H). 1-244 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 9.25 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-245 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.16 (s, 1H), 7.76 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-246 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.36 (s, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.19 (s, 3H). 1-247 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.16 (s, 3H), 3.67 (s, 2H). 1-248 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 7.91 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-249 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.89 (d, J = 5.5 Hz, 1H), 7.93 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H), 2.49 (s, 3H). 1-250 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 9.17 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 1.50 (p, J = 8.0 Hz, 1H), 1.19-1.15 (m, 2H), 1.05-1.01 (m, 2H). 1-251 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.27 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-252 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.20 (s, 3H) 1-253 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 7.96 (s, 1H), 7.72 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-254 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-255 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.30 (s, 1H), 7.67 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.29 (s, 3H). 1-256 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-257 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-258 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-259 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-260 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 10.15 (s, 2H), 8.82 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-261 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 9.87 (d, J = 1.5 Hz, 1H), 9.50 (d, J = 5.0 Hz, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.29 (dd, J = 5.0, 1.5 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-262 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 9.35 (dd, J = 5.0, 1.5 Hz, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.68 (dd, J = 7.5, 1.5 Hz, 1H), 7.99- 7.92 (m, 2H), 4.33 (s, 3H). 1-263 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 9.06 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.78 (d, J = 5.0 Hz, 1H), 8.00 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-264 Cl

1-265 Cl

1-266 Cl

1-267 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.94 (dd, J = 7.5, 1.5 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 7.59 (dd, J = 7.5, 1.5 Hz, 1H), 7.53 (s, 1H), 7.40 (td, J = 7.5, 1.5 Hz, 1H), 7.35 (td, J = 7.5, 1.5 Hz, 1H), 4.33 (s, 3H). 1-268 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 2.0 Hz, 1H), 7.92 (d, J = 1.5 Hz, 1H), 7.81 (dd, J = 7.5, 1.5 Hz, 1H), 7.76-7.69 (m, 2H), 7.04 (d, J = 2.0, 1H), 4.33 (s, 3H). 1-269 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 7.66 (d, J = 2.0 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 7.47 (d, J = 1.5 Hz, 1H), 7.17 (d, J = 1.5 Hz, 1H), 6.91 (d, J = 2.0 Hz, 1H), 4.33 (s, 3H), 3.02 (s, 6H). 1-270 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.03 (s, 1H), 9.32 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.60 (d, J = 1.5 Hz, 1H), 8.08 (d, J = 7.5 Hz, 1H), 7.95 (dd, J = 7.5, 1.5 Hz, 1H), 7.72 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-271 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.18 (dd, J = 7.5, 1.5 Hz, 1H), 8.08 (dd, J = 7.5, 1.5 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.58-7.54 (m, 1H), 7.50-7.46 (m, 1H), 4.33 (s, 3H). 1-272 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 9.46 (s, 1H), 8.99-8.95 (m, 2H), 8.73 (d, J = 5.0 Hz, 1H), 7.62 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-273 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.58 (s, 1H), 8.10 (d, J = 7.5 Hz, 1H), 7.80 (d, J = 7.5 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.84 (s, 3H). 1-274 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.53 (s, 1H), 7.98 (d, J = 1.5 Hz, 1H), 7.73 (d, J = 7.5 Hz, 1H), 7.67 (dd, J = 7.5, 1.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-275 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 7.98-7.89 (m, 2H), 7.87-7.84 (m, 1H), 7.64-7.59 (m, 2H), 4.33 (s, 3H). 1-276 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 1.5 Hz, 1H), 7.37 (d, J = 1.5 Hz, 1H), 5.32 (s, 1H), 4.50 (s, 2H), 4.33 (s, 3H), 4.02 (s, 3H), 2.34 (s, 3H). 1-277 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 8.17 (dd, J = 7.5, 1.5 Hz, 1H), 7.83 (dd, J = 7.5, 1.5 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.37 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H), 3.79 (s, 3H). 1-278 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.28 (d, J = 1.5 Hz, 1H), 8.16 (d, J = 7.5, 1.5 Hz, 1H), 8.05 (s, 1H), 7.80 (d, J = 7.5 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.79 (s, 3H). 1-279 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 5.0 Hz, 1H), 7.64-7.54 (m, 2H), 7.47 (d, J = 1.5 Hz, 1H), 4.33 (s, 3H), 2.51 (s, 3H). 1-280 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.39 (s, 1H), 8.07 (dd, J = 7.5, 1.5 Hz, 1H), 7.64 dd, J = 7.5, 1.5 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.45 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-281 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.39 (d, J = 7.5 Hz, 1H), 7.88-7.79 (m, 2H), 7.64 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-282 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 9.27 (d, J = 1.5 Hz, 1H), 8.96 (d, J = 5.0 Hz, 1H), 8.69 (d, J = 1.5 Hz, 1H), 8.15-8.05 (m, 2H), 7.87 (d, J = 5.0 Hz, 1H), 7.69 (td, J = 7.5, 1.5 Hz, 1H), 7.58 (td, J = 7.5, 1.5 Hz, 1H), 4.33 (s, 3H). 1-283 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 13.19 (s, 1H), 12.08 (s, 1H), 9.79 (d, J = 1.5 Hz, 1H), 9.21 (d, J = 1.5 Hz, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.44 (dd, J = 7.5, 1.5 Hz, 1H), 8.33 (dd, J = 7.5, 1.5 Hz, 1H), 8.12 (t, J = 7.5 Hz, 1H), 7.85 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-284 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 9.73 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.49-8.41 (m, 2H), 8.35 (dd, J = 7.5, 1.5 Hz, 1H), 7.93 (d, J = 7.5 Hz, 1H), 7.74 (t, J = 7.5 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-285 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 9.69 (s, 1H), 9.04 (d, J = 5.0 Hz, 1H), 8.43 (d, J = 1.5 Hz, 1H), 8.07-7.97 (m, 3H), 4.33 (s, 3H), 3.85 (s, 1H). 1-286 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 9.13 (d, J = 5.5 Hz, 1H), 8.91-8.83 (m, 2H), 8.23 (dd, J = 7.5, 1.5 Hz, 2H), 7.93 (t, J = 7.5 Hz, 1H), 7.65 (d, J = 5.5 Hz, 1H), 4.33 (s, 3H). 1-287 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.91-8.86 (m, 3H), 8.74 (d, J = 1.5 Hz, 1H), 8.29-8.21 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-288 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.28 (dd, J = 7.5, 1.5 Hz, 1H), 7.93 (d, J = 7.5 Hz, 1H), 7.80 (d, J = 1.5 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.05 (s, 1H), 4.33 (s, 3H), 3.62 (s, 3H), 3.55 (s, 2H), 2.18 (s, 3H). 1-289 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.77 (d, J = 1.5 Hz, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.24 (dd, J = 7.5, 1.5 Hz, 1H), 7.74-7.68 (m, 2H), 7.17 (d, J = 7.5 Hz, 1H), 6.63 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H), 3.79 (s, 3H). 1-290 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.00-7.92 (m, 2H), 7.73 (dd, J = 7.5, 1.5 Hz, 1H), 7.47 (td, J = 7.5, 1.5 Hz, 1H), 7.31 (td, J = 7.5, 1.5 Hz, 1H), 7.14 (s, 1H), 4.33 (s, 3H), 3.82 (s, 3H). 1-291 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 7.97 (d, J = 7.5 Hz, 1H), 7.95-7.88 (m, 3H), 7.39 (dd, J = 7.5, 1.5 Hz, 1H), 4.33 (s, 3H). 1-292 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.04 (dd, J = 7.5, 1.5 Hz, 1H), 7.91 (dd, J = 7.5, 1.5 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 7.65 (d, J = 2.5 Hz, 1H), 7.56 (t, J = 7.5 Hz, 1H), 7.44 (d, J = 2.5 Hz, 1H), 4.33 (s, 3H). 1-293 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.07-7.97 (m, 2H), 7.75 (d, J = 5.0 Hz, 1H), 7.66-7.56 (m, 2H), 7.50 (t, J = 7.5 Hz, 1H), 4.33 (s, 3H). 1-294 Cl

1-295 Cl

1-296 Cl

1-297 Cl

1-298 Cl

1-299 Cl

1-300 Cl

1-301 Cl

1-302 Cl

1-303 Cl

1-304 Cl

1-305 Cl

1-306 Cl

1-307 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 7.65-7.57 (m, 2H), 7.25 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 4.40-4.32 (m, 2H), 1.50 (t, J = 8.0 Hz, 3H). 1-308 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.25 (t, J = 5.0 Hz, 2H), 1.74-1.70 (m, 2H), 0.89 (t, J = 8.0 Hz, 3H). 1-309 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.56 (s, 1H), 12.06 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.05- 7.97 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H). 1-310 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.49 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.07-6.04 (m, 1H), 5.41-5.32 (m, 1H), 5.27- 5.16 (m, 1H), 4.43-4.37 (m, 2H). 1-311 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 5.57 (s, 2H), 3.35 (s, 3H). 1-312 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.10 (t, J = 8.0 Hz, 2H), 2.92 (t, J = 8.0 Hz, 2H), 2.09 (s, 3H). 1-313 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 5.05 (s, 2H), 3.78 (s, 3H). 1-314 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.07-7.99 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 7.59-7.53 (m, 4H), 7.52-7.49 (m, 1H), 7.35-7.27 (m, 2H). 1-315 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.06-7.99 (m, 2H), 7.69-7.60 (m, 3H), 7.57-7.54 (m, 2H), 7.35-7.27 (m, 2H). 1-316 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.59 (d, J = 5.0 Hz, 1H), 7.41 (dd, J = 7.5, 1.5 Hz, 2H), 7.35-7.27 (m, 2H), 7.08-7.02 (m, 2H), 5.45 (s, 2H). 1-317 Cl CH₃

1-318 Cl

1-319 Cl

1-320 Cl

1-321 Cl

1-322 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 7.64 (d, J = 5.0 Hz, 1H), 6.14-6.07 (m, 1H), 3.91 (s, 3H), 3.36-3.30 (m, 2H), 3.05 (t, J = 7.0, Hz, 2H), 2.60 (t, J = 7.0 Hz, 2H), 2.20 (s, 3H). 1-323 Cl

1-324 Cl

1-325 Cl

1-326 Cl

1-327 Cl

1-328 Cl

1-329 Cl

1-330 Cl

1-331 Cl

1-332 Cl

1-333 Cl

1-334 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.23 (s, 1H), 7.64- 7.57 (m, 2H), 7.25 (d, J = 5.0 Hz, 1H), 7.11- 7.03 (m, 2H), 3.95 (s, 3H). 1-335 Cl

1-336 Cl

1-337 Cl

1-338 Cl

1-339 Cl

1-340 Cl

1-341 Cl

1-342 Cl

1-343 Cl

1-344 Cl

1-345 Cl

1-346 Cl

1-347 Cl

1-348 Cl

1-349 Cl

1-350 Cl

1-351 Cl

1-352 Cl

1-353 Cl

1-354 Cl

1-355 Cl

1-356 Cl

1-357 Cl

1-358 Cl

1-359 Cl

1-360 Cl

1-361 Cl

1-362 Cl

1-363 Cl

1-364 Cl

1-365 Cl

1-366 Cl

1-367 Cl

1-368 Cl

1-369 Cl

1-370 Cl

1-371 Cl

1-372 Cl

1-373 Cl

1-374 Cl

1-375 Cl

1-376 Cl

1-377 Cl

1-378 Cl

1-379 Cl

1-380 Cl

1-381 Cl

1-382 Cl

1-383 Cl

1-384 Cl

1-385 Cl

1-386 Cl

1-387 Cl

1-388 Cl

1-389 Cl

1-390 Cl

1-391 Cl

1-392 Cl

1-393 Cl

1-394 Cl

1-395 Cl

1-396 Cl

1-397 Cl

1-398 Cl

1-399 Cl

1-400 Cl

1-401 Cl

1-402 Cl

1-403 Cl

1-404 Cl

1-405 Cl

1-406 Cl

1-407 Cl

1-408 Cl

1-409 Cl

1-410 Cl

1-411 Cl

1-412 Cl

1-413 Cl

1-414 Cl

1-415 Cl

1-416 Cl

1-417 Cl

1-418 Cl

1-419 Cl

1-420 Cl

1-421 Cl

1-422 Cl

1-423 Cl

1-424 Cl

1-425 Cl

1-426 Cl

1-427 Cl

1-428 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.38-8.35 (m, 2H), 8.18- 8.07 (m, 2H), 8.03-8.00 (m, 1H), 7.90 (t, J = 8.5 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.59-7.56 (m, 1H), 7.52-7.50 (m, 1H), 4.31 (s, 3H). 1-429 Cl

1-430 Cl

1-431 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 9.29 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.59 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.26-8.22 (m, 2H), 8.17-8.14 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 3.92 (s, 3H). 1-432 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.93-8.85 (m, 2H), 8.81-8.74 (m, 1H), 8.43- 8.36 (m, 2H), 8.02-7.99 (m, 2H), 7.74-7.60 (m, 5H), 3.92 (s, 3H). 1-433 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.51 (s, 1H), 8.20 (dd, J = 7.5, 2.0 Hz, 1H), 8.07-8.03 (m, 2H), 7.67 (d, J = 5.0 Hz, 1H), 7.65-7.58 (m, 2H), 7.44-7.41 (m, 1H), 7.35-7.32 (m, 1H), 3.96 (s, 3H). 1-434 Cl

1-435 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.90 (d, J = 5.0 Hz, 1H), 8.55 (d, J = 2.0 Hz, 1H), 8.48 (dd, J = 7.5, 2.0 Hz, 1H), 8.39 (d, J = 7.5 Hz, 1H), 8.32 (s, 1H), 8.11-8.05 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.56 (td, J = 7.5, 2.0 Hz, 1H), 7.48 (td, J = 7.5, 2.0 Hz, 1H), 3.92 (s, 3H). 1-436 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.13 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.58-8.48 (m, 2H), 8.29 (s, 1H), 7.74 (td, J = 7.5, 2.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.24-7.22 (m, 1H), 3.91 (s, 3H). 1-437 Cl

1-438 Cl

1-439 Cl

1-440 Cl

1-441 Cl

1-442 Cl

1-443 Cl

1-444 Cl

1-445 Cl

1-446 Cl

1-447 Cl

1-448 Cl

1-449 Cl

1-450 Cl

1-451 Cl

1-452 Cl

1-453 Cl

1-454 Cl

1-455 Cl

1-456 Cl

1-457 Cl

1-458 Cl

1-459 Cl

1-460 Cl

1-461 Cl

1-462 Cl

1-463 Cl

1-464 Cl

1-465 Cl

1-466 Cl

1-467 Cl

1-468 Cl

1-469 Cl

1-470 Cl

1-471 Cl

1-472 Cl

1-473 Cl

1-474 Cl

1-475 Cl

1-476 Cl

1-477 Cl

1-478 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 9.25 (s, 2H), 8.83 (d, J = 5.0 Hz, 1H), 8.31 (s, 1H), 7.75 (d, J = 5.0 Hz, 1H), 3.91 (s, 3H), 3.85 (s, 3H). 1-479 Cl

1-480 Cl

1-481 Cl

1-482 Cl

1-483 Cl

1-484 Cl

1-485 Cl

1-486 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 6.87 (s, 1H), 3.93 (s, 3H), 3.92 (s, 3H), 2.41 (s, 3H). 1-487 Cl

1-488 Cl

1-489 Cl

1-490 Cl

1-491 Cl

1-492 Cl

1-493 Cl

1-494 Cl

1-495 Cl

1-496 Cl

1-497 Cl

1-498 Cl

1-499 Cl

1-500 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.37 (s, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.67 (s, 1H), 7.49 (d, J = 2.0 Hz, 1H), 6.69 (d, J = 2.0 Hz, 1H), 3.92 (s, 3H). 1-501 Cl

1-502 Cl

1-503 Cl

1-504 Cl

1-505 Cl

1-506 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.37 (s, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.52 (d, J = 2.0 Hz, 1H), 7.13 (d, J = 2.0 Hz, 1H), 3.92 (s, 3H). 1-507 Cl

1-508 Cl

1-509 Cl

1-510 Cl

1-511 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 8.36 (s, 1H), 7.98-7.90 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.33 (s, 3H), 2.52 (s, 3H). 1-512 F

1-513 Br

1-514

1-515 CF₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.36 (s, 1H), 8.02- 7.95 (m, 2H), 7.58 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.01 (s, 3H). 1-516

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34 (s, 1H), 8.00- 7.93 (m, 2H), 7.69-7.60 (m, 3H), 7.47-7.35 (m, 3H), 7.35-7.27 (m, 2H), 3.83 (s, 3H). 1-517

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 8.09- 8.01 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.03 (s, 3H), 3.67 (s, 3H). 1-518

1-519

1-520

1-521

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.04- 7.97 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.02 (s, 3H), 3.00 (q, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H). 1-522

1-523

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.31 (s, 1H), 8.04- 7.97 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.03 (s, 3H), 2.63-2.61 (m, 1H), 2.58-5.56 (m, 1H), 1.20 (t, J = 8.0 Hz, 3H). 1-524

1-525

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.06- 7.98 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.98 (s, 3H), 2.80 (s, 6H). 1-526

1-527 Et

1-528

1-529 NO₂

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 8.35 (s, 1H), 7.98- 7.91 (m, 2H), 7.72 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.26 (s, 3H). 1-530 CN

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 9.01 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.05- 7.97 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.92 (s, 3H). 1-531

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.37 (s, 1H), 8.03- 7.95 (m, 2H), 7.65 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.68 (s, 2H), 4.33 (s, 3H), 3.28 (s, 3H). 1-532

1-533

1-534

1-535

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.61 (d, J = 5.0 Hz, 1H), 8.03-7.96 (m, 2H), 7.35-7.25 (m, 3H), 6.53 (dd, J = 16.5, 10.0 Hz, 1H), 5.60-5.67 (m, 1H), 5.31 5.29 (m, 1H), 4.33 (s, 3H). 1-536

1-537

¹H NMR (500 MHz, DMSO-d₆) δ 12.15 (s, 1H), 9.01 (d, J = 5.0 Hz, 1H), 8.33 (s, 1H), 8.05- 7.97 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.03 (s, 3H), 3.92 (s, 1H). 1-538

1-539

1-540

1-541 Cl

1-542 Cl

1-543 Cl

1-544 Cl

1-545 Cl

1-546 Cl

1-547 Cl

1-548 Cl

1-549 Cl

1-550 Cl

1-551 Cl

1-552 Cl

1-553 Cl

1-554 Cl

1-555 Cl

1-556 Cl

1-557 Cl

1-558 Cl

1-559 Cl

1-560 Cl

1-561 Cl

1-562 Cl

1-563 Cl

1-564 Cl

1-565 Cl

1-566 Cl

1-567 Cl

1-568 Cl

1-569 Cl

1-570 Cl

1-571 Cl

1-572 Cl

1-573 Cl

1-574 Cl

1-575 Cl

1-576 Cl

1-577 Cl

1-578 Cl

1-579 Cl

1-580 Cl

1-581 Cl

1-582 Cl

1-583 Cl

1-584 Cl

1-585 Cl

1-586 Cl

1-587 Cl

1-588 Cl

1-589 Cl

1-590 Cl

1-591 Cl

1-592 Cl

1-593 Cl

1-594 Cl

1-595 Cl

1-596 Cl

1-597 Cl

1-598 Cl

1-599 Cl

1-600 Cl

1-601 Cl

1-602 Cl

1-603 Cl

1-604 Cl

1-605 Cl

1-606 Cl

1-607 Cl

1-608 Cl

1-609 Cl

1-610 Cl

1-611 Cl

1-612 Cl

1-613 Cl

1-614 Cl

1-615 Cl

1-616 Cl

1-617 Cl

1-618 Cl

1-619 Cl

1-620 Cl

1-621 Cl

1-622 Cl

1-623 Cl

1-624 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.16 (s, 1H), 10.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04- 7.96 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 2.45 (s, 3H). 1-625 Cl

1-626 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.61 (s, 3H), 2.18 (p, J = 7.0 Hz, 1H), 1.13 (m, 2H), 0.88 (m, 2H). 1-627 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.46 (hept, J = 8.0 Hz, 1H), 1.65 (d, J = 8.0 Hz, 6H). 1-628 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.03-7.96 (m, 2H), 7.67 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.32 (s, 2H), 3.94 (s, 3H), 2.99 (s, 3H). 1-629 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.08-8.00 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.93 (s, 3H), 3.59 (s, 3H), 3.51 (s, 2H). 1-630 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.11-8.02 (m, 4H), 7.65 (d, J = 5.0 Hz, 1H), 7.54-7.46 (m, 1H), 7.48-7.40 (m, 2H), 7.35-7.27 (m, 2H), 3.97 (s, 3H). 1-631 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.89 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 4.40 (q, J = 8.0 Hz, 2H), 1.49 (t, J = 8.0 Hz, 3H). 1-632 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.13 (s, 1H), 10.06 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.70 (dd, J = 5.0, 2.0 Hz, 1H), 8.46-8.44 (m, 2H), 8.11- 8.03 (m, 2H), 7.64 (d, J = 5.0 Hz, 1H), 7.57 (dd, J = 8.0, 2.0 Hz, 1H), 7.35-7.27 (m, 2H), . 1-633 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.08-8.00 (m, 2H), 7.63 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.94 (s, 3H), 3.63 (t, J = 8.0 Hz, 4H), 3.36 (t, J = 8.0 Hz, 4H). 1-634 Cl CH₃

1-635 Cl

1-636 Cl

1-637 Cl

1-638 Cl

1-639 Cl

1-640 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.12 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.84 (d, J = 5.0 Hz, 1H), 6.26-6.19 (m, 1H), 4.23-4.17 (m, 2H), 3.86 (s, 3H), 3.79 (t, J = 5.0 Hz, 2H), 2.50 (s, 3H), 2.40 (t, J = 5.0, 2H). 1-641 Cl

1-642 Cl

1-643 Cl

1-644 Cl

1-645 Cl

1-646 Cl

1-647 Cl

1-648 Cl

1-649 Cl

1-650 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.12 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.88 (s, 3H), 2.50 (s, 3H). 1-651 Cl

1-652 Cl

1-653 Cl

1-654 Cl

1-655 Cl

1-656 Cl

1-657 Cl

1-658 Cl

1-659 Cl

1-660 Cl

1-661 Cl

1-662 Cl

1-663 Cl

1-664 Cl

1-665 Cl

1-666 Cl

1-667 Cl

1-668 Cl

1-669 Cl

1-670 Cl

1-671 Cl

1-672 Cl

1-673 Cl

1-674 Cl

1-675 Cl

1-676 Cl

1-677 Cl

1-678 Cl

1-679 Cl

1-680 Cl

1-681 Cl

1-682 Cl

1-683 Cl

1-684 Cl

1-685 Cl

1-686 Cl

1-687 Cl

1-688 Cl

1-689 Cl

1-690 Cl

1-691 Cl

1-692 Cl

1-693 Cl

1-694 Cl

1-695 Cl

1-696 Cl

1-697 Cl

1-698 Cl

1-699 Cl

1-700 Cl

1-701 Cl

1-702 Cl

1-703 Cl

1-704 Cl

1-705 Cl

1-706 Cl

1-707 Cl

1-708 Cl

1-709 Cl

1-710 Cl

1-711 Cl

1-712 Cl

1-713 Cl

1-714 Cl

1-715 Cl

1-716 Cl

1-717 Cl

1-718 Cl

1-719 Cl

1-720 Cl

1-721 Cl

1-722 Cl

1-723 Cl

1-724 Cl

1-725 Cl

1-726 Cl

1-727 Cl

1-728 Cl

1-729 Cl

1-730 Cl

1-731 Cl

1-732 Cl

1-733 Cl

1-734 Cl

1-735 Cl

1-736 Cl

1-737 Cl

1-738 Cl

1-739 Cl

1-740 Cl

1-741 Cl

1-742 Cl

1-743 Cl

1-744 Cl

1-745 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 8.35 (dd, J = 7.5, 2.0 Hz, 1H), 8.13-8.10 (m, 2H), 8.04 (dt, J = 7.5, 2.0 Hz, 1H), 7.94-7.85 (m, 2H), 7.59 (td, J = 7.5, 2.0 Hz, 1H), 7.52 (td, J = 7.5, 2.00 Hz, 1H), 3.88 (s, 3H), 2.51 (s, 3H). 1-746 Cl

1-747 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 9.28 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.60 (d, J = 5.5 Hz, 1H), 8.20-8.17 (m, 2H), 7.89-7.78 (m, 3H), 3.87 (s, 3H), 2.51 (s, 3H). 1-748 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.93-8.86 (m, 2H), 8.78 (dd, J = 8.0, 2.5 Hz, 1H), 8.38 (s, 1H), 8.05-7.94 (m, 2H), 7.83 (d, J = 5.0 Hz, 1H), 7.74-7.60 (m, 4H), 3.88 (s, 3H), 2.51 (s, 3H). 1-749 Cl

1-750 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.21 (dd, J = 7.5, 2.0 Hz, 1H), 8.05-8.03 (m, 2H), 7.85 (d, J = 5.0 Hz, 1H), 7.66-7.58 (m, 2H), 7.44 (td, J = 7.5, 2.0 Hz, 1H), 7.35 (td, J = 7.5, 2.0 Hz, 1H), 3.88 (s, 3H), 2.52 (s, 3H). 1-751 Cl

1-752 Cl

1-753 Cl

1-754 Cl

1-755 Cl

1-756 Cl

1-757 Cl

1-758 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.91 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 5.0 Hz, 1H), 3.87 (s, 3H), 2.50 (s, 3H), 2.48 (s, 3H). 1-759 Cl

1-760 Cl

1-761 Cl

1-762 Cl

1-763 Cl

1-764 Cl

1-765 Cl

1-766 Cl

1-767 Cl

1-768 Cl

1-769 Cl

1-770 Cl

1-771 Cl

1-772 Cl

1-773 Cl

1-774 Cl

1-775 Cl

1-776 Cl

1-777 Cl

1-778 Cl

1-779 Cl

1-780 Cl

1-781 Cl

1-782 Cl

1-783 Cl

1-784 Cl

1-785 Cl

1-786 Cl

1-787 Cl

1-788 Cl

1-789 Cl

1-790 Cl

1-791 Cl

1-792 Cl

1-793 Cl

1-794 Cl

1-795 Cl

1-796 Cl

1-797 Cl

1-798 Cl

1-799 Cl

1-800 Cl

1-801 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.80 (s, 1H), 6.97 (s, 1H), 3.92 (s, 3H), 3.87 (s, 3H), 2.51 (s, 3H). 1-802 Cl

1-803 Cl

1-804 Cl

1-805 Cl

1-806 Cl

1-807 Cl

1-808 Cl

1-809 Cl

1-810 Cl

1-811 Cl

1-812 Cl

1-813 Cl

1-814 Cl

1-815 Cl

1-816 Cl

1-817 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.26 (d, J = 2.0 Hz, 1H), 6.98 (t, J = 2.0 Hz, 1H), 3.86 (s, 3H), 2.51 (s, 3H). 1-818 Cl

1-819 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 7.98 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 2.0 Hz, 1H), 7.47 (d, J = 2.0 Hz, 1H), 7.15 (t, J = 2.0 Hz, 1H), 3.86 (s, 3H), 2.51 (s, 3H). 1-820 Cl

1-821 Cl

1-822 Cl

1-823 Cl

1-824 Cl

1-825 Cl

1-826 Cl

1-827 CH₃

1-828 F

1-829 Br

1-830

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 7.95-7.87 (m, 2H), 7.37 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.87 (s, 3H), 2.85 (hept, J = 7.0 Hz, 1H), 2.50 (s, 3H), 1.11 (d, J = 7.0 Hz, 6H). 1-831 CF₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.58 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.89 (s, 3H), 2.51 (s, 3H). 1-832

1-833

1-834

¹H NMR (500 MHz, DMSO-d₆) δ 12.33 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 8.10-8.02 (m, 2H), 7.94 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.10 (q, J = 8.0 Hz, 2H), 3.88 (s, 3H), 2.51 (s, 3H), 1.34 (t, J = 8.0 Hz, 3H). 1-835

1-836

1-837

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.88 (s, 3H), 3.00 (q, J = 8.0 Hz, 2H), 2.50 (s, 3H), 1.19 (t, J = 8.0 Hz, 3H). 1-838

1-839

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.87 (s, 3H), 2.61-2.59 (m, 1H), 2.57-2.55 (m, 1H) 2.50 (s, 3H), 1.20 (t, J = 8.0 Hz, 3H). 1-840

1-841

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.07-8.00 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.87 (s, 3H), 2.76 (s, 6H), 2.49 (s, 3H). 1-842

1-843 Et

1-844

1-845 NO₂

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 7.99-7.91 (m, 2H), 7.71 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.89 (s, 3H), 2.52 (s, 3H). 1-846 CN

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 9.02 (d, J = 5.0 Hz, 1H), 8.06-7.98 (m, 2H), 7.73 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.89 (s, 3H), 2.51 (s, 3H). 1-847

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 3.88 (s, 3H), 3.28 (s, 3H), 2.51 (s, 3H). 1-848

1-849

1-850

1-851

1-852

1-853

1-854

1-855

1-856

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.60-7.52 (m, 2H), 7.35-7.27 (m, 2H), 7.23-7.15 (m, 2H), 3.79 (s, 3H), 2.49 (s, 3H). 1-857 Cl

1-858 Cl

1-859 Cl

1-860 Cl

1-861 Cl

1-862 Cl

1-863 Cl

1-864 Cl

1-865 Cl

1-866 Cl

1-867 Cl

1-868 Cl

1-869 Cl

1-870 Cl

1-871 Cl

1-872 Cl

1-873 Cl

1-874 Cl

1-875 Cl

1-876 Cl

1-877 Cl

1-878 Cl

1-879 Cl

1-880 Cl

1-881 Cl

1-882 Cl

1-883 Cl

1-884 Cl

1-885 Cl

1-886 Cl

1-887 Cl

1-888 Cl

1-889 Cl

1-890 Cl

1-891 Cl

1-892 Cl

1-893 Cl

1-894 Cl

1-895 Cl

1-896 Cl

1-897 Cl

1-898 Cl

1-899 Cl

1-900 Cl

1-901 Cl

1-902 Cl

1-903 Cl

1-904 Cl

1-905 Cl

1-906 Cl

1-907 Cl

1-908 Cl

1-909 Cl

1-910 Cl

1-911 Cl

1-912 Cl

1-913 Cl

1-914 Cl

1-915 Cl

1-916 Cl

1-917 Cl

1-918 Cl

1-919 Cl

1-920 Cl

1-921 Cl

1-922 Cl

1-923 Cl

1-924 Cl

1-925 Cl

1-926 Cl

1-927 Cl

1-928 Cl

1-929 Cl

1-930 Cl

1-931 Cl

1-932 Cl

1-933 Cl

1-934 Cl

1-935 Cl

1-936 Cl

1-937 Cl

1-938 Cl

1-939 Cl

1-940 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 9.15 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03- 7.95 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.82 (s, 3H). 1-941 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.02-7.95 (m, 2H), 7.74 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.07 (q, J = 8.0 Hz, 2H), 1.29 (t, J = 8.0 Hz, 3H). 1-942 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.73 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.01 (s, 3H), 3.88 (s, 3H). 1-943 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.68 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.18 (t, J = 8.0 Hz, 2H), 3.96 (t, J = 8.0 Hz, 2H), 3.58 (s, 3H), 2.47 (s, 3H). 1-944 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.10 (s, 1H), 10.40 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.05- 7.97 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.36 (t, J = 5.5 Hz, 4H), 1.62- 1.56 (m, 2H), 1.51 (p, J = 7.0 Hz, 4H). 1-945 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.94 (d, J = 5.0 Hz, 1H), 8.05-7.93 (m, 4H), 7.83 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.14-7.08 (m, 2H), 3.86 (s, 3H), 3.79 (s, 3H). 1-946 Cl CH₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.94 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 2.59 (s, 3H), 2.46 (s, 3H). 1-947 Cl

1-948 Cl

1-949 Cl

1-950 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.66 (d, J = 5.0 Hz, 1H), 6.18 (t, J = 6.0 Hz, 1H), 2.44 (s, 3H), 2.13-1.92 (m, 4H), 1.76-1.58 (m, 2H), 1.48-1.35 (m, 2H). 1-951 Cl

1-952 Cl

1-953 Cl

1-954 Cl

1-955 Cl

1-956 Cl

1-957 Cl

1-958 Cl

1-959 Cl

1-960 Cl

1-961 Cl

1-962 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.63-7.55 (m, 2H), 7.12-7.03 (m, 3H), 2.38 (s, 3H). 1-963 Cl

1-964 Cl

1-965 Cl

1-966 Cl

1-967 Cl

1-968 Cl

1-969 Cl

1-970 Cl

1-971 Cl

1-972 Cl

1-973 Cl

1-974 Cl

1-975 Cl

1-976 Cl

1-977 Cl

1-978 Cl

1-979 Cl

1-980 Cl

1-981 Cl

1-982 Cl

1-983 Cl

1-984 Cl

1-985 Cl

1-986 Cl

1-987 Cl

1-988 Cl

1-989 Cl

1-990 Cl

1-991 Cl

1-992 Cl

1-993 Cl

1-994 Cl

1-995 Cl

1-996 Cl

1-997 Cl

1-998 Cl

1-999 Cl

1-1000 Cl

1-1001 Cl

1-1002 Cl

1-1003 Cl

1-1004 Cl

1-1005 Cl

1-1006 Cl

1-1007 Cl

1-1008 Cl

1-1009 Cl

1-1010 Cl

1-1011 Cl

1-1012 Cl

1-1013 Cl

1-1014 Cl

1-1015 Cl

1-1016 Cl

1-1017 Cl

1-1018 Cl

1-1019 Cl

1-1020 Cl

1-1021 Cl

1-1022 Cl

1-1023 Cl

1-1024 Cl

1-1025 Cl

1-1026 Cl

1-1027 Cl

1-1028 Cl

1-1029 Cl

1-1030 Cl

1-1031 Cl

1-1032 Cl

1-1033 Cl

1-1034 Cl

1-1035 Cl

1-1036 Cl

1-1037 Cl

1-1038 Cl

1-1039 Cl

1-1040 Cl

1-1041 Cl

1-1042 Cl

1-1043 Cl

1-1044 Cl

1-1045 Cl

1-1046 Cl

1-1047 Cl

1-1048 Cl

1-1049 Cl

1-1050 Cl

1-1051 Cl

1-1052 Cl

1-1053 Cl

1-1054 Cl

1-1055 Cl

1-1056 Cl

1-1057 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.52 (d, J = 1.5 Hz, 1H), 8.17 (dd, J = 7.5, 1.5 Hz, 1H), 8.09-7.99 (m, 3H), 7.67-7.58 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 2.44 (s, 3H). 1-1058 Cl

1-1059 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 9.26 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.59 (d, J = 5.5 Hz, 1H), 8.22-8.13 (m, 2H), 7.86-7.79 (m, 2H), 7.60 (d, J = 5.0 Hz, 1H), 2.46 (s, 3H). 1-1060 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.90 (dd, J = 7.5, 1.5 Hz, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.81-8.73 (m, 1H), 8.38 (d, J = 1.5 Hz, 1H), 8.09-7.97 (m, 2H), 7.74-7.59 (m, 5H), 2.48 (s, 3H). 1-1061 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.20 (dd, J = 7.5, 1.5 Hz, 1H), 8.15-8.01 (m, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.64-7.57 (m, 2H), 7.48-7.41 (m, 1H), 7.39-7.26 (m, 1H), 2.45 (s, 3H). 1-1062 Cl

1-1063 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.52 (d, J = 1.5 Hz, 1H), 8.47 (dd, J = 7.5, 1.5 Hz, 1H), 8.38 (d, J = 7.5 Hz, 1H), 8.16-8.02 (m, 2H), 7.60-7.52 (m, 2H), 7.53-7.42 m, 1H), 2.44 (s, 3H). 1-1064 Cl

1-1065 Cl

1-1066 Cl

1-1067 Cl

1-1068 Cl

1-1069 Cl

1-1070 Cl

1-1071 Cl

1-1072 Cl

1-1073 Cl

1-1074 Cl

1-1075 Cl

1-1076 Cl

1-1077 Cl

1-1078 Cl

1-1079 Cl

1-1080 Cl

1-1081 Cl

1-1082 Cl

1-1083 Cl

1-1084 Cl

1-1085 Cl

1-1086 Cl

1-1087 Cl

1-1088 Cl

1-1089 Cl

1-1090 Cl

1-1091 Cl

1-1092 Cl

1-1093 Cl

1-1094 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 8.31 (dd, J = 5.5, 5.0 Hz, 1H), 8.16-8.01 (m, 1H), 7.88-7.85 (m, 1H), 7.73 (d, J = 5.0 Hz, 1H), 2.44 (s, 3H). 1-1095 Cl

1-1096 Cl

1-1097 Cl

1-1098 Cl

1-1099 Cl

1-1100 Cl

1-1101 Cl

1-1102 Cl

1-1103 Cl

1-1104 Cl

1-1105 Cl

1-1106 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 9.48 (s, 2H), 8.80 (d, J = 5.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 3.85 (s, 3H), 2.44 (s, 3H). 1-1107 Cl

1-1108 Cl

1-1109 Cl

1-1110 Cl

1-1111 Cl

1-1112 Cl

1-1113 Cl

1-1114 Cl

1-1115 Cl

1-1116 Cl

1-1117 Cl

1-1118 Cl

1-1119 Cl

1-1120 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.25 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.84 (t, J = 65.0 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 6.98 (s, 1H), 2.45 (s, 3H), 2.39 (s, 3H). 1-1121 Cl

1-1122 Cl

1-1123 Cl

1-1124 Cl

1-1125 Cl

1-1126 Cl

1-1127 Cl

1-1128 Cl

1-1129 Cl

1-1130 Cl

1-1131 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 9.17 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 7.49-7.32 (m, 1H), 6.38-6.27 (m, 1H), 2.63 (s, 3H). 1-1132 Cl

1-1133 Cl

1-1134 Cl

1-1135 Cl

1-1136 Cl

1-1137 Cl

1-1138 Cl

1-1139 Cl

1-1140 Cl

1-1141 CH₃

1-1142 F

1-1143 Br

1-1144

1-1145 CF₃

¹H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.00-7.93 (m, 2H), 7.48 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.45 (s, 3H). 1-1146

1-1147

¹H NMR (500 MHz, DMSO-d6) δ 12.11 (s, 1H), 8.53 (d, J = 5.0 Hz, 1H), 8.06-7.98 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.64 (s, 3H), 2.45 (s, 3H). 1-1148

1-1149

1-1150

¹H NMR (500 MHz, DMSO-d6) δ 12.60 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.41 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.45 (s, 3H), 2.20 (s, 3H). 1-1151

1-1152

¹H NMR (500 MHz, DMSO-d6) δ 12.03 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.97-7.89 (m, 2H), 7.40 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.45 (s, 3H), 2.37 (s, 3H). 1-1153

1-1154

1-1155

¹H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.35 (d, J = 5.0 Hz, 1H), 7.95-7.88 (m, 1H), 7.46 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.72 (s, 6H), 2.44 (s, 3H). 1-1156

1-1157 Et

¹H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.07-7.81 (m, 2H), 7.52-7.20 (m, 3H), 2.70 (q, J = 8.0 Hz, 2H), 2.45 (s, 3H), 1.07 (t, J = 8.0 Hz, 3H). 1-1158

1-1159 NO₂

¹H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.95-7.87 (m, 2H), 7.62 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.47 (s, 3H). 1-1160 CN

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.98 (d, J = 5.0 Hz, 1H), 8.02-7.95 (m, 2H), 7.64 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.46 (s, 3H). 1-1161

1-1162

1-1163

1-1164

1-1165

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.01-7.94 (m, 2H), 7.40 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 3.58 (q, J = 8.0 Hz, 2H), 2.45 (s, 3H), 1.18 (t, J = 8.0 Hz, 3H). 1-1166

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.35-7.27 (m, 2H), 7.19 (d, J = 5.0 Hz, 1H), 6.62-6.48 (m, 1H), 5.48-5.36 (m, 1H), 5.30-5.22 (m, 1H), 2.43 (s, 3H). 1-1167

1-1168

1-1169

1-1170

1-1171

¹H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 7.98-7.91 (m, 2H), 7.57-7.47 (m, 3H), 7.35-7.27 (m, 2H), 7.23- 7.15 (m, 2H), 2.43 (s, 3H). 1-1172 Cl

1-1173 Cl

1-1174 Cl

1-1175 Cl

1-1176 Cl

1-1177 Cl

1-1178 Cl

1-1179 Cl

1-1180 Cl

1-1181 Cl

1-1182 Cl

1-1183 Cl

1-1184 Cl

1-1185 Cl

1-1186 Cl

1-1187 Cl

1-1188 Cl

1-1189 Cl

1-1190 Cl

1-1191 Cl

1-1192 Cl

1-1193 Cl

1-1194 Cl

1-1195 Cl

1-1196 Cl

1-1197 Cl

1-1198 Cl

1-1199 Cl

1-1200 Cl

1-1201 Cl

1-1202 Cl

1-1203 Cl

1-1204 Cl

1-1205 Cl

1-1206 Cl

1-1207 Cl

1-1208 Cl

1-1209 Cl

1-1210 Cl

1-1211 Cl

1-1212 Cl

1-1213 Cl

1-1214 Cl

1-1215 Cl

1-1216 Cl

1-1217 Cl

1-1218 Cl

1-1219 Cl

1-1220 Cl

1-1221 Cl

1-1222 Cl

1-1223 Cl

1-1224 Cl

1-1225 Cl

1-1226 Cl

1-1227 Cl

1-1228 Cl

1-1229 Cl

1-1230 Cl

1-1231 Cl

1-1232 Cl

1-1233 Cl

1-1234 Cl

1-1235 Cl

1-1236 Cl

1-1237 Cl

1-1238 Cl

1-1239 Cl

1-1240 Cl

1-1241 Cl

1-1242 Cl

1-1243 Cl

1-1244 Cl

1-1245 Cl

1-1246 Cl

1-1247 Cl

1-1248 Cl

1-1249 Cl

1-1250 Cl

1-1251 Cl

1-1252 Cl

1-1253 Cl

1-1254 Cl

1-1255 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.01 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.76 (s, 1H), 7.60 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H). 1-1256 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.02 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.78 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.08 (hept, J = 7.0 Hz, 1H), 1.26 (d, J = 7.0 Hz, 6H). 1-1257 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.75 (d, J = 4.5 Hz, 1H), 7.68-7.60 (m, 2H), 7.11-7.03 (m, 2H), 6.79 (d, J = 4.5 Hz, 1H), 1.50-1.35 (m, 1H), 1.02-0.96 (m, 2H), 0.94- 0.88 (m, 2H). 1-1258 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1259 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1260 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.79 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.70 (s, 2H), 2.10 (s, 3H). 1-1261 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 13.02 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.15 (s, 2H), 8.01- 7.93 (m, 2H), 7.80 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H). 1-1262 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 13.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.81 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.38 (s, 3H). 1-1263 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.78 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.48 (hept, J = 7.0 Hz, 1H), 1.21 (d, J = 7.0 Hz, 6H). 1-1264 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.34 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.89 (d, J = 5.0 Hz, 1H), 7.72 (s, 1H), 7.48 (d, J = 7.5 Hz, 1H), 7.42 (d, J = 7.5 Hz, 1H), 7.35- 7.27 (m, 2H). 1-1265 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.10-7.98 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.37-7.19 (m, 4H), 6.72-6.95 (m, 1H), 6.90-6.80 (m, 2H). 1-1266 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.07-7.92 (m, 2H), 7.74-7.72 (m, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.37- 7.25 (m, 2H), 6.84-6.82 (m, 1H), 6.68 (t, J = 7.5 Hz, 1H). 1-1267 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.08-7.95 (m, 2H), 7.77 (d, J = 2.5, 1H), 7.66 (d, J = 2.5 Hz, 1H), 7.46 (d, J = 5.0 Hz, 1H), 7.37-7.25 (m, 2H), 6.66 (t, J = 2.5 Hz, 1H). 1-1268 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.10-7.96 (m, 2H), 7.79-7.62 (m, 2H), 7.58 (d, J = 5.0 Hz, 1H), 7.38- 7.20 (m, 4H), 4.07 (q, J = 8.0 Hz, 2H), 3.97 (t, J = 8.0 Hz, 3H). 1-1269 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.07-7.92 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 7.40-7.24 (m, 2H), 3.58-3.40 (m, 4H), 1.81-1.68 (m, 4H), 1.59-1.43 (m, 2H). 1-1270 Cl CH₃

1-1271 Cl

1-1272 Cl

1-1273 Cl

1-1274 Cl

1-1275 Cl

1-1276 Cl

1-1277 Cl

1-1278 Cl

1-1279 Cl

1-1280 Cl

1-1281 Cl

1-1282 Cl

1-1283 Cl

1-1284 Cl

1-1285 Cl

1-1286 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.53 (s, 1H), 8.79-8.73 (m, 2H), 7.64-7.57 (m, 2H), 7.33 (d, J = 4.5 Hz, 1H), 7.11-7.03 (m, 2H), 6.77 (d, J = 2.5 Hz, 1H). 1-1287 Cl

1-1288 Cl

1-1289 Cl

1-1290 Cl

1-1291 Cl

1-1292 Cl

1-1293 Cl

1-1294 Cl

1-1295 Cl

1-1296 Cl

1-1297 Cl

1-1298 Cl

1-1299 Cl

1-1300 Cl

1-1301 Cl

1-1302 Cl

1-1303 Cl

1-1304 Cl

1-1305 Cl

1-1306 Cl

1-1307 Cl

1-1308 Cl

1-1309 Cl

1-1310 Cl

1-1311 Cl

1-1312 Cl

1-1313 Cl

1-1314 Cl

1-1315 Cl

1-1316 Cl

1-1317 Cl

1-1318 Cl

1-1319 Cl

1-1320 Cl

1-1321 Cl

1-1322 Cl

1-1323 Cl

1-1324 Cl

1-1325 Cl

1-1326 Cl

1-1327 Cl

1-1328 Cl

1-1329 Cl

1-1330 Cl

1-1331 Cl

1-1332 Cl

1-1333 Cl

1-1334 Cl

1-1335 Cl

1-1336 Cl

1-1337 Cl

1-1338 Cl

1-1339 Cl

1-1340 Cl

1-1341 Cl

1-1342 Cl

1-1343 Cl

1-1344 Cl

1-1345 Cl

1-1346 Cl

1-1347 Cl

1-1348 Cl

1-1349 Cl

1-1350 Cl

1-1351 Cl

1-1352 Cl

1-1353 Cl

1-1354 Cl

1-1355 Cl

1-1356 Cl

1-1357 Cl

1-1358 Cl

1-1359 Cl

1-1360 Cl

1-1361 Cl

1-1362 Cl

1-1363 Cl

1-1364 Cl

1-1365 Cl

1-1366 Cl

1-1367 Cl

1-1368 Cl

1-1369 Cl

1-1370 Cl

1-1371 Cl

1-1372 Cl

1-1373 Cl

1-1374 Cl

1-1375 Cl

1-1376 Cl

1-1377 Cl

1-1378 Cl

1-1379 Cl

1-1380 Cl

1-1381 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.54 (t, J = 1.5 Hz, 1H), 8.19 (dd, J = 7.5, 1.5 Hz, 1H), 8.14-7.92 (m, 3H), 7.88 (d, J = 5.0 Hz, 1H), 7.67-7.58 (m, 2H), 6.77 (d, J = 2.5 Hz, 1H). 1-1382 Cl

1-1383 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 9.26 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 5.5 Hz, 1H), 8.60-8.58 (m, 1H), 8.23 (dd, J = 7.5, 1.5 Hz, 1H), 8.17-8.14 (m, 1H), 7.87-7.82 (m, 2H), 7.66 (d, J = 2.5 Hz, 1H), 6.77 (d, J = 2.5 Hz, 1H). 1-1384 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.94-8.85 (m, 2H), 8.81-8.73 (m, 2H), 8.40 (d, J = 1.5 Hz, 1H), 8.20-8.13 (m, 1H), 8.05- 7.99 (m, 1H), 7.95-7.86 (m, 5H), 6.77 (d, J = 2.5 Hz, 1H). 1-1385 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.21 (dd, J = 7.5, 1.5 Hz, 1H), 8.13-7.98 (m, 2H), 7.91 (d, J = 5.0 Hz, 1H), 7.66-7.58 (m, 2H), 7.44 (td, J = 7.5, 1.5 Hz, 1H), 7.38-7.22 (m, 1H), 6.77 (d, J = 7.5 Hz, 1H). 1-1386 Cl

1-1387 Cl

1-1388 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.21 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 7.5 Hz, 1H), 8.25-8.12 (m, 2H), 8.05-7.88 (m, 2H), 7.72- 7.62 (m, 2H), 7.60-7.55 (m, 1H), 7.48-7.21 (m, 1H), 6.77 (d, J = 2.5 Hz, 1H). 1-1389 Cl

1-1390 Cl

1-1391 Cl

1-1392 Cl

1-1393 Cl

1-1394 Cl

1-1395 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.18 (s, 1H), 8.90 (s, 1H), 8.77-8.61 (m, 2H), 8.46 (d, J = 5.0 Hz, 1H), 8.02 (d, J = 2.5 Hz, 1H), 7.43 (d, J = 5.0 Hz, 1H), 6.77 (d, J = 2.5 Hz, 1H), 2.42 (s, 3H). 1-1396 Cl

1-1397 Cl

1-1398 Cl

1-1399 Cl

1-1400 Cl

1-1401 Cl

1-1402 Cl

1-1403 Cl

1-1404 Cl

1-1405 Cl

1-1406 Cl

1-1407 Cl

1-1408 Cl

1-1409 Cl

1-1410 Cl

1-1411 Cl

1-1412 Cl

1-1413 Cl

1-1414 Cl

1-1415 Cl

1-1416 Cl

1-1417 Cl

1-1418 Cl

1-1419 Cl

1-1420 Cl

1-1421 Cl

1-1422 Cl

1-1423 Cl

1-1424 Cl

1-1425 Cl

1-1426 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 9.37-9.33 (m, 3H), 8.83 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 2.5 Hz, 1H), 7.99 (d, J = 5.0 Hz, 1H), 6.77 (d, J = 2.5 Hz, 1H). 1-1427 Cl

1-1428 Cl

1-1429 Cl

1-1430 Cl

1-1431 Cl

1-1432 Cl

1-1433 Cl

1-1434 Cl

1-1435 Cl

1-1436 Cl

1-1437 Cl

1-1438 Cl

1-1439 Cl

1-1440 Cl

1-1441 Cl

1-1442 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.17 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 2.5 Hz, 1H), 7.97 (d, J = 5.0 Hz, 1H), 7.80 (s, 1H), 6.97 (s, 1H), 6.77 (d, J = 2.5 Hz, 1H), 4.29 (q, J = 8.0 Hz, 2H), 1.16 (t, J = 8.0 Hz, 3H). 1-1443 Cl

1-1444 Cl

1-1445 Cl

1-1446 Cl

1-1447 Cl

1-1448 Cl

1-1449 Cl

1-1450 Cl

1-1451 Cl

1-1452 Cl

1-1453 Cl

1-1454 Cl

1-1455 Cl

1-1456 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.76 (d, J = 2.5 Hz, 1H), 8.03 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 2.5 Hz, 1H), 7.47 (d, J = 4.0 Hz, 1H), 7.15-7.12 (m, 1H), 6.77 (d, J = 2.5 Hz, 1H). 1-1457 Cl

1-1458 Cl

1-1459 Cl

1-1460 Cl

1-1461 Cl

1-1462 Cl

1-1463 Cl

1-1464 CH₃

¹H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 7.98-7.90 (m, 2H), 7.85 (s, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.51 (s, 3H), 2.35 (s, 3H). 1-1465 F

1-1466 Br

1-1467

1-1468 CF₃

¹H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.84 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.31 (s, 3H). 1-1469

¹H NMR (500 MHz, DMSO-d6) δ 12.15 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.83 (s, 1H), 7.69-7.59 (m, 3H), 7.47-7.40 (m, 2H), 7.39-7.21 (m, 1H), 7.35-7.27 (m, 2H), 2.23 (s, 3H). 1-1470

¹H NMR (500 MHz, DMSO-d6) δ 12.12 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.09-8.01 (m, 2H), 7.85 (s, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 3.67 (s, 3H), 2.31 (s, 3H). 1-1471

1-1472

1-1473

1-1474

¹H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.58 (d, J = 4.9 Hz, 1H), 8.03-7.96 (m, 2H), 7.85 (s, 1H), 7.47 (d, J = 4.9 Hz, 1H), 7.35-7.27 (m, 2H), 3.00 (q, J = 8.0 Hz, 2H), 2.31 (s, 3H), 1.19 (t, J = 8.0 Hz, 3H). 1-1475

1-1476

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.14-8.06 (m, 2H), 7.86 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.63-2.61 (m, 1H), 2.59-2.56 (m, 1H), 2.31 (s, 3H), 1.22 (t, J = 8.0 Hz, 3H). 1-1477

1-1478

1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 8.06-7.98 (m, 2H), 7.83 (s, 1H), 7.48 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.75 (s, 6H), 2.30 (s, 3H). 1-1479

1-1480 Et

1-1481

1-1482 NO₂

1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 7.99-7.91 (m, 2H), 7.86 (s, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.31 (s, 3H). 1-1483 CN

1H NMR (500 MHz, DMSO-d6) δ 12.13 (s, 1H), 9.01 (d, J = 5.0 Hz, 1H), 8.05-7.97 (m, 2H), 7.84 (s, 1H), 7.69 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.31 (s, 3H). 1-1484

1H NMR (500 MHz, DMSO-d6) δ 12.09 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.03-7.96 (m, 2H), 7.84 (s, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.68 (s, 2H), 3.28 (s, 3H), 2.30 (s, 3H). 1-1485

1-1486

1-1487

1-1488

1-1489

1-1490

1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.01-7.94 (m, 2H), 7.80 (s, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.31 (s, 1H), 2.39 (s, 3H). 1-1491

1-1492

1-1493

1-1494 Cl

1-1495 Cl

1-1496 Cl

1-1497 Cl

1-1498 Cl

1-1499 Cl

1-1500 Cl

1-1501 Cl

1-1502 Cl

1-1503 Cl

1-1504 Cl

1-1505 Cl

1-1506 Cl

1-1507 Cl

1-1508 Cl

1-1509 Cl

1-1510 Cl

1-1511 Cl

1-1512 Cl

1-1513 Cl

1-1514 Cl

1-1515 Cl

1-1516 Cl

1-1517 Cl

1-1518 Cl

1-1519 Cl

1-1520 Cl

1-1521 Cl

1-1522 Cl

1-1523 Cl

1-1524 Cl

1-1525 Cl

1-1526 Cl

1-1527 Cl

1-1528 Cl

1-1529 Cl

1-1530 Cl

1-1531 Cl

1-1532 Cl

1-1533 Cl

1-1534 Cl

1-1535 Cl

1-1536 Cl

1-1537 Cl

1-1538 Cl

1-1539 Cl

1-1540 Cl

1-1541 Cl

1-1542 Cl

1-1543 Cl

1-1544 Cl

1-1545 Cl

1-1546 Cl

1-1547 Cl

1-1548 Cl

1-1549 Cl

1-1550 Cl

1-1551 Cl

1-1552 Cl

1-1553 Cl

1-1554 Cl

1-1555 Cl

1-1556 Cl

1-1557 Cl

1-1558 Cl

1-1559 Cl

1-1560 Cl

1-1561 Cl

1-1562 Cl

1-1563 Cl

1-1564 Cl

1-1565 Cl

1-1566 Cl

1-1567 Cl

1-1568 Cl

1-1569 Cl

1-1570 Cl

1-1571 Cl

1-1572 Cl

1-1573 Cl

1-1574 Cl

1-1575 Cl

1-1576 Cl

1-1577 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.76 (d, J = 5.0 Hz, 1H), 7.78 (s, 1H), 7.63-7.56 (m, 2H), 7.41 (d, J = 5.0 Hz, 1H), 7.11-7.03 (m, 2H), 2.31 (s, 3H). 1-1578 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.76 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.70 (q, J = 8.0 Hz, 2H), 1.25 (t, J = 8.0 Hz, 3H). 1-1579 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 8.10 (s, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.46-2.32 (m, 1H), 1.12-1.02 (m, 2H), 0.85-0.69 (m, 2H). 1-1580 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.85 (s, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 4.64 (s, 2H). 1-1581 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 3H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1582 Cl

1H NMR (500 MHz, DMSO-d6) δ 11.99 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.51 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.82 (s, 1H), 4.63 (s, 2H), 3.33 (s, 3H). 1-1583 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.72 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1584 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.43 (s, 1H), 10.68 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.04- 7.96 (m, 2H), 7.50 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 5.88 (s, 1H), 3.47 (q, J = 8.0 Hz, 2H), 1.07 (t, J = 8.0 Hz, 3H). 1-1585 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.11 (s, 1H), 8.07-7.99 (m, 2H), 7.65-7.58 (m, 3H), 7.58-7.52 (m, 2H), 7.35-7.27 (m, 2H). 1-1586 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 9.00 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 8.07-7.99 (m, 2H), 7.86-7.79 (m, 2H), 7.73-7.65 (m, 1H), 7.66-7.56 (m, 3H), 7.35-7.27 (m, 2H). 1-1587 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.83 (d, J = 5.0 Hz, 1H), 8.73-8.58 (m, 1H), 8.07- 8.00 (m, 2H), 7.97 (dd, J = 8.0, 1.0 Hz, 1H), 7.86-7.69 (m, 1H), 7.63 (d, J = 5.0 Hz, 1H), 7.48-7.36 (m, 1H), 7.35-7.27 (m, 2H), 6.74 (s, 1H). 1-1588 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.06 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.30 (s, 1H), 8.05-7.97 (m, 2H), 7.70 (d, J = 2.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.19-7.09 (m, 2H). 1-1589 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.07 (s, 1H), 8.85 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.32 (s, 1H), 8.28 (s, 1H), 8.05-7.98 (m, 2H), 7.53 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1590 Cl CH₃

1-1591 Cl

1-1592 Cl

1-1593 Cl

1-1594 Cl

1-1595 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 7.44 (d, J = 2.5 Hz, 1H), 7.25 (d, J = 2.5 Hz, 1H), 6.42-6.36 (m, 1H), 4.34 (t, J = 6.0 Hz, 2H), 3.33-3.31 (m, 2H), 3.05-3.01 (m, 2H), 1.96 (s, 3H). 1-1596 Cl

1-1597 Cl

1-1598 Cl

1-1599 Cl

1-1600 Cl

1-1601 Cl

1-1602 Cl

1-1603 Cl

1-1604 Cl

1-1605 Cl

1-1606 Cl

1-1607 Cl

1H NMR (500 MHz, DMSO-d6) δ 12.24 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.56-7.48 (m, 2H), 7.35-7.27 (m, 2H), 7.23 (d, J = 2.5 Hz, 1H). 1-1608 Cl

1-1609 Cl

1-1610 Cl

1-1611 Cl

1-1612 Cl

1-1613 Cl

1-1614 Cl

1-1615 Cl

1-1616 Cl

1-1617 Cl

1-1618 Cl

1-1619 Cl

1-1620 Cl

1-1621 Cl

1-1622 Cl

1-1623 Cl

1-1624 Cl

1-1625 Cl

1-1626 Cl

1-1627 Cl

1-1628 Cl

1-1629 Cl

1-1630 Cl

1-1631 Cl

1-1632 Cl

1-1633 Cl

1-1634 Cl

1-1635 Cl

1-1636 Cl

1-1637 Cl

1-1638 Cl

1-1639 Cl

1-1640 Cl

1-1641 Cl

1-1642 Cl

1-1643 Cl

1-1644 Cl

1-1645 Cl

1-1646 Cl

1-1647 Cl

1-1648 Cl

1-1649 Cl

1-1650 Cl

1-1651 Cl

1-1652 Cl

1-1653 Cl

1-1654 Cl

1-1655 Cl

1-1656 Cl

1-1657 Cl

1-1658 Cl

1-1659 Cl

1-1660 Cl

1-1661 Cl

1-1662 Cl

1-1663 Cl

1-1664 Cl

1-1665 Cl

1-1666 Cl

1-1667 Cl

1-1668 Cl

1-1669 Cl

1-1670 Cl

1-1671 Cl

1-1672 Cl

1-1673 Cl

1-1674 Cl

1-1675 Cl

1-1676 Cl

1-1677 Cl

1-1678 Cl

1-1679 Cl

1-1680 Cl

1-1681 Cl

1-1682 Cl

1-1683 Cl

1-1684 Cl

1-1685 Cl

1-1686 Cl

1-1687 Cl

1-1688 Cl

1-1689 Cl

1-1690 Cl

1-1691 Cl

1-1692 Cl

1-1693 Cl

1-1694 Cl

1-1695 Cl

1-1696 Cl

1-1697 Cl

1-1698 Cl

1-1699 Cl

1-1700 Cl

1-1701 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.12 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.39 (dd, J = 7.5, 2.0 Hz, 1H), 8.15-8.07 (m, 2H), 8.03-8.01 (m, 1H), 7.90 (t, J = 7.5 Hz, 1H), 7.64 (d, J = 5.0 Hz, 1H), 7.60-7.56 (m, 1H), 7.52-7.50 (m, 1H), 7.47 (d, J = 2.0 Hz, 1H), 7.25 (d, J = 2.0 Hz, 1H). 1-1702 Cl

1-1703 Cl

1-1704 Cl

1-1705 Cl

1-1706 Cl

1-1707 Cl

1-1708 Cl

1-1709 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.89 (d, J = 5.0 Hz, 1H), 8.63 (s, 1H), 8.48 (dd, J = 7.5, 2.0 Hz, 1H), 8.15-8.10 (m, 2H), 8.07-8.04 (m, 1H), 7.61 (d, J = 5.0 Hz, 1H), 7.56-7.54 (m, 1H), 7.49-7.46 (m, 1H), 7.45 (d, J = 2.5 Hz, 1H), 7.25 (d, J = 2.5 Hz, 1H). 1-1710 Cl

1-1711 Cl

1-1712 Cl

1-1713 Cl

1-1714 Cl

1-1715 Cl

1-1716 Cl

1-1717 Cl

1-1718 Cl

1-1719 Cl

1-1720 Cl

1-1721 Cl

1-1722 Cl

1-1723 Cl

1-1724 Cl

1-1725 Cl

1-1726 Cl

1-1727 Cl

1-1728 Cl

1-1729 Cl

1-1730 Cl

1-1731 Cl

1-1732 Cl

1-1733 Cl

1-1734 Cl

1-1735 Cl

1-1736 Cl

1-1737 Cl

1-1738 Cl

1-1739 Cl

1-1740 Cl

1-1741 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.13 (s, 1H), 8.02 (d, J = 5.0 Hz, 1H), 7.76 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 2.5 Hz, 1H), 7.24 (d, J = 2.5 Hz, 1H). 1-1742 Cl

1-1743 Cl

1-1744 Cl

1-1745 Cl

1-1746 Cl

1-1747 Cl

1-1748 Cl

1-1749 Cl

1-1750 Cl

1-1751 Cl

1-1752 Cl

1-1753 Cl

1-1754 Cl

1-1755 Cl

1-1756 Cl

1-1757 Cl

1-1758 Cl

1-1759 Cl

1-1760 Cl

1-1761 Cl

1-1762 Cl

1-1763 Cl

1-1764 Cl

1-1765 Cl

1-1766 Cl

1-1767 Cl

1-1768 Cl

1-1769 Cl

1-1770 Cl

1-1771 Cl

1-1772 Cl

1-1773 Cl

1-1774 Cl

1-1775 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 2.5 Hz, 1H), 7.26 (d, J = 2.5 Hz, 1H), 7.24 (d, J = 2.5 Hz, 1H), 6.69 (d, J = 2.5 Hz, 1H), 3.92 (s, 3H). 1-1776 Cl

1-1777 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.86 (d, J = 5.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 7.50 (d, J = 2.5 Hz, 1H), 7.28-7.22 (m, 2H), 6.98 (t, J = 2.5 Hz, 1H). 1-1778 Cl

1-1779 Cl

1-1780 Cl

1-1781 Cl

1-1782 Cl

1-1783 Cl

1-1784 Cl

1-1785 Cl

1-1786 Cl

1-1787 CH₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.00-7.92 (m, 2H), 7.52 (d, J = 2.5 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.22 (d, J = 2.5 Hz, 1H), 2.44 (s, 3H). 1-1788 F

1-1789 Br

1-1790

1-1791 CF₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.55-7.48 (m, 2H), 7.35-7.27 (m, 2H), 7.21 (d, J = 2.5 Hz, 1H). 1-1792

¹H NMR (500 MHz, DMSO-d₆) δ 12.13 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.67-7.61 (m, 3H), 7.49-7.35 (m, 4H), 7.35- 7.27 (m, 2H), 7.23 (d, J = 2.5 Hz, 1H). 1-1793

1-1794

1-1795

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.53 (d, J = 5.0 Hz, 1H), 8.10-8.02 (m, 2H), 7.52 (d, J = 2.5 Hz, 1H), 7.45 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.21 (d, J = 2.5 Hz, 1H), 5.03 (s, 2H). 1-1796

1-1797

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.46 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.25 (d, J = 2.5 Hz, 1H), 3.00 (q, J = 8.0 Hz, 2H), 1.19 (t, J = 8.0 Hz, 3H). 1-1798

1-1799

¹H NMR (500 MHz, DMSO-d₆) δ 12.34 (s, 1H), 8.81 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.24 (d, J = 7.5 Hz, 1H), 2.61-2.59 (m, 1H), 2.57-2.55 (m, 1H), 1.21 (t, J = 8.0 Hz, 3H). 1-1800

1-1801

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.36 (d, J = 5.0 Hz, 1H), 8.07-8.00 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.42 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.24 (d, J = 2.5 Hz, 1H), 2.77 (s, 6H). 1-1802

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.93 (d, J = 5.0 Hz, 1H), 7.51 (d, J = 2.5 Hz, 1H), 7.35-7.27 (m, 2H), 7.26 (d, J = 2.5 Hz, 1H), 2.35 (s, 6H). 1-1803 Et

1-1804

1-1805 NO₂

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.01-7.93 (m, 2H), 7.73 (d, J = 5.0 Hz, 1H), 7.47 (d, J = 2.5 Hz, 1H), 7.34-7.29 (m, 2H), 7.27 (d, J = 2.5 Hz, 1H). 1-1806 CN

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 9.02 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.46 (d, J = 2.5 Hz, 1H), 7.37-7.27 (m, 2H), 7.25 (d, J = 2.5 Hz, 1H). 1-1807

¹H NMR (500 MHz, DMSO-d₆) δ 12.12 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.51 (d, J = 2.5 Hz, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.20 (d, J = 2.5 Hz, 1H), 4.68 (s, 2H), 3.28 (s, 3H). 1-1808

1-1809

1-1810

1-1811

1-1812

1-1813

1-1814

1-1815

1-1816

1-1817 Cl

1-1818 Cl

1-1819 Cl

1-1820 Cl

1-1821 Cl

1-1822 Cl

1-1823 Cl

1-1824 Cl

1-1825 Cl

1-1826 Cl

1-1827 Cl

1-1828 Cl

1-1829 Cl

1-1830 Cl

1-1831 Cl

1-1832 Cl

1-1833 Cl

1-1834 Cl

1-1835 Cl

1-1836 Cl

1-1837 Cl

1-1838 Cl

1-1839 Cl

1-1840 Cl

1-1841 Cl

1-1842 Cl

1-1843 Cl

1-1844 Cl

1-1845 Cl

1-1846 Cl

1-1847 Cl

1-1848 Cl

1-1849 Cl

1-1850 Cl

1-1851 Cl

1-1852 Cl

1-1853 Cl

1-1854 Cl

1-1855 Cl

1-1856 Cl

1-1857 Cl

1-1858 Cl

1-1859 Cl

1-1860 Cl

1-1861 Cl

1-1862 Cl

1-1863 Cl

1-1864 Cl

1-1865 Cl

1-1866 Cl

1-1867 Cl

1-1868 Cl

1-1869 Cl

1-1870 Cl

1-1871 Cl

1-1872 Cl

1-1873 Cl

1-1874 Cl

1-1875 Cl

1-1876 Cl

1-1877 Cl

1-1878 Cl

1-1879 Cl

1-1880 Cl

1-1881 Cl

1-1882 Cl

1-1883 Cl

1-1884 Cl

1-1885 Cl

1-1886 Cl

1-1887 Cl

1-1888 Cl

1-1889 Cl

1-1890 Cl

1-1891 Cl

1-1892 Cl

1-1893 Cl

1-1894 Cl

1-1895 Cl

1-1896 Cl

1-1897 Cl

1-1898 Cl

1-1899 Cl

1-1900 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.34 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.25 (s, 1H), 2.65 (t, J = 8.0 Hz, 2H), 1.70-1.48 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H). 1-1901 Cl

¹H NMR (500 MHz, DMSO-d6) δ 12.14 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.75 (d, J = 5.0 Hz, 1H), 7.36 (s, 1H), 7.35-7.27 (m, 2H). 1-1902 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.14 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.06-7.99 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 6.81 (s, 1H), 3.81 (s, 3H). 1-1903 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.03-7.95 (m, 2H), 7.70 (d, J = 5.0 Hz, 1H), 7.45 (s, 1H), 7.35- 7.27 (m, 2H), 2.40 (s, 3H). 1-1904 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.04 (s, 1H), 8.95 (d, J = 5.0 Hz, 1H), 8.34-8.26 (m, 2H), 7.69 (d, J = 5.0 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H). 1-1905 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.69 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H), 3.20 (s, 6H). 1-1906 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.07 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.74 (s, 1H), 7.55 (d, J = 5.0 Hz, 1H), 7.35- 7.27 (m, 2H). 1-1907 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.09 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.04-7.96 (m, 2H), 7.56 (d, J = 5.0 Hz, 1H), 7.46 (s, 1H), 7.35- 7.27 (m, 2H), 3.83 (s, 2H), 2.60 (s, 3H). 1-1908 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.11 (s, 1H), 10.52 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.06- 7.99 (m, 2H), 7.69 (s, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 2.13 (s, 3H). 1-1909 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.08 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.66 (d, J = 5.5 Hz, 2H), 8.05-8.01 (m, 2H), 7.99 (d, J = 5.5, 2H), 7.79 (s, 1H), 7.71 (d, J = 5.0 H,z 1H), 7.35- 7.27 (m, 2H). 1-1910 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.05 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.20-8.13 (m, 2H), 7.90 (s, 1H), 7.66 (d, J = 5.0 Hz, 1H), 7.64-7.60 (m, 2H), 7.55-7.51 (m, 2H), 7.35-7.27 (m, 2H). 1-1911 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.06 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.35-7.27 (m, 2H), 7.22 (s, 1H), 5.08 (t, J = 7.0 Hz, 1H), 3.90-3.79 (m, 2H), 2.26-2.11 (m, 2H), 1.88-1.76 (m, 2H). 1-1912 OMe CH₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.84 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.90 (d, J = 5.0 Hz, 1H), 3.74 (s, 3H), 2.51 (s, 3H), 2.46 (s, 3H). 1-1913 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 6.99-6.94 (m, 1H), 6.13-6.09 (m, 1H), 5.63-5.59 (m, 1H), 4.33 (s, 3H). 1-1914 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.33 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.77 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H), 3.70 (t, J = 6.0 Hz, 2H), 2.43 (t, J = 7.5 Hz, 2H), 2.11-2.06 (m, 2H). 1-1915 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.74-7.70 (m, 2H), 7.49 (d, J = 5.0 Hz, 1H), 7.27-7.23 (m, 2H), 4.31 (s, 3H), 2.74-2.69 (m, 2H), 1.19 (t, J = 8.0 Hz, 3H). 1-1916 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.72-7.69 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.40-7.37 (m, 2H), 4.36 (s, 3H), 2.89-2.84 (m, 1H), 1.20 (d, J = 7.0 Hz, 6H). 1-1917 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.35 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.88-7.85 (m, 1H), 7.81-7.79 (m, 1H), 7.63-7.60 (m, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.34-7.31 (m, 1H), 4.39 (s, 3H), 2.63 (t, J = 5.5 Hz, 2H), 1.56-1.51 (m, 2H), 1.32-1.28 (m, 2H), 0.89 (t, J = 8.0 Hz, 3H). 1-1918 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.71-7.68 (m, 2H), 7.48-7.45 (m, 3H), 6.73-6.70 (m, 1H), 5.96- 5.93 (m, 1H), 5.71-5.68 (m, 1H), 4.32 (s, 3H). 1-1919 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.30 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.81-7.75 (m, 2H), 7.65-7.59 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 6.45 (t, J = 57.0 Hz, 1H), 4.32 (s, 3H). 1-1920 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.02 (s, 1H), 7.88-7.85 (m, 1H), 7.68-7.65 (m, 1H), 7.59-7.57 (m, 1H), 7.48 (d, J = 5.0 Hz, 1H), 4.99 (s, 2H), 4.33 (s, 3H). 1-1921 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.80-7.77 (m, 2H), 7.48 (d, J = 5.0 Hz, 1H), 7.04-7.01 (m, 2H), 4.38 (s, 3H), 3.99 (t, J = 7.5 Hz, 2H), 1.78-1.71 (m, 2H), 0.98 (t, J = 8.0 Hz, 3H). 1-1922 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.85-7.79 (m, 2H), 7.55-7.49 (m, 3H), 4.39 (s, 3H), 2.45 (s, 3H). 1-1923 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.68-7.65 (m, 2H), 7.47 (d, J = 5.0 Hz, 1H), 7.21-7.17 (m, 2H), 4.38 (s, 3H). 1-1924 Cl

1-1925 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.89-7.82 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 7.51-7.45 (m, 2H), 4.30 (s, 3H), 2.87 (s, 6H). 1-1926 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.73-7.70 (m, 2H), 7.53-7.50 (m, 1H), 7.16-7.14 (m, 1H), 4.31 (s, 3H), 2.27 (s, 3H), 2.23 (s, 3H). 1-1927 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.53-7.50 (m, 1H), 7.33-7.26 (m, 2H), 4.38 (s, 3H). 1-1928 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.88-7.85 (m, 1H), 7.56-7.53 (m, 1H), 7.47 (d, J = 5.0 Hz, 1H), 7.22-7.19 (m, 1H), 4.39 (s, 3H). 1-1929 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.65-7.62 (m, 2H), 7.54-7.51 (m, 1H), 7.27-7.23 (m, 1H), 4.38 (s, 3H). 1-1930 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.69-7.62 (m, 2H), 7.62-7.59 (m, 1H), 7.53 (d, J = 5.0 Hz, 1H), 4.25 (s, 3H). 1-1931 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.60-7.57 (m, 1H), 7.49 (d, J = 5.0 Hz, 1H), 7.19-7.16 (m, 1H), 7.12-7.09 (m, 1H), 4.29 (s, 3H), 2.37 (s, 3H). 1-1932 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 7.5 Hz, 1H), 7.68 (d, J = 5.0 Hz, 1H), 7.56-7.53 (m, 1H), 7.10-7.07 (m, 1H), 4.30 (s, 3H), 2.31 (s, 3H). 1-1933 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.20 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.75 (s, 1H), 7.67- 7.64 (m, 2H), 6.94 (d, J = 7.5 Hz, 1H), 4.39 (s, 3H), 3.74 (s, 3H), 2.15 (s, 3H). 1-1934 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.73 (d, J = 6.0 Hz, 1H), 8.10 (s, 1H), 8.02 (s, 1H), 7.75 (s, 1H), 7.56 (d, J = 5.0 Hz, 1H), 4.29 (s, 3H), 2.32 (s, 3H). 1-1935 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.07 (d, J = 2.0 Hz, 1H), 7.72 (dd, J = 7.5, 2.0 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 7.5 Hz, 1H), 4.37 (s, 3H), 2.25 (s, 3H). 1-1936 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.33 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.11 (d, J = 2.0 Hz, 1H), 7.96 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H), 2.45 (s, 3H). 1-1937 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 7.5 Hz, 1H), 7.76-7.72 (m, 1H), 7.61-7.55 (m, 2H), 4.29 (s, 3H), 2.39 (s, 3H). 1-1938 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.05-7.98 (m, 2H), 7.74 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 7.5 Hz, 1H), 4.35 (s, 3H), 2.45 (s, 3H). 1-1939 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 8.27 (dd, J = 7.5, 2.0 Hz, 1H), 7.74 (dd, J = 7.5, 2.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.40 (dd, J = 7.5, 7.5 Hz, 1H), 4.36 (s, 3H), 2.45 (s, 3H). 1-1940 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.96-7.92 (m, 1H), 7.68-7.65 (m, 1H), 7.48-7.43 (m, 2H), 4.30 (s, 3H). 1-1941 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.91-7.87 (m, 2H), 7.65 (d, J = 5.0 Hz, 1H), 7.53-7.50 (m, 1H), 4.37 (s, 3H). 1-1942 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.31 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 8.20 (s, 1H), 8.06-8.03 (m, 1H), 7.66 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 7.5 Hz, 1H), 4.35 (s, 3H). 1-1943 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.17-8.14 (m, 1H), 7.61-7.55 (m, 2H), 7.49 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H). 1-1944 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.88 (s, 1H), 7.74- 7.70 (m, 2H), 7.59 (s, 1H), 4.35 (s, 3H). 1-1945 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.31 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.81-7.78 (m, 1H), 7.46 (d, J = 5.0 Hz, 1H), 6.79-6.76 (m, 1H), 6.74-6.72 (m, 1H), 4.31 (s, 3H), 3.76 (s, 3H). 1-1946 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.47-7.44 (m, 2H), 7.25-7.22 (m, 2H), 4.35 (s, 3H), 3.80 (s, 3H). 1-1947 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.78-7.75 (m, 1H), 7.63 (d, J = 5.0 Hz, 1H), 6.92-6.89 (m, 1H), 6.80-6.77 (m, 1H), 4.38 (q, J = 8.0 Hz, 2H), 4.35 (s, 3H), 1.45 (t, J = 8.0 Hz, 3H). 1-1948 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.48-7.44 (m, 2H), 7.05-7.01 (m, 1H), 6.90-6.87 (m, 1H), 4.39 (s, 3H), 3.70 (d, J = 7.0 Hz, 2H), 2.01-1.92 (m, 1H), 0.95 (d, J = 7.0 Hz, 6H). 1-1949 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.94 (s, 1H), 7.65 (d, J = 5.0 Hz, 1H), 7.48 (d, J = 7.5 Hz, 1H), 6.93 (d, J = 7.5 Hz, 1H), 4.33 (s, 3H), 3.85 (s, 3H). 1-1950 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.67-7.63 (m, 2H), 7.55 (d, J = 7.5 Hz, 1H), 4.31 (s, 3H), 4.10 (q, J = 8.0 Hz, 2H), 1.34 (t, J = 8.0 Hz, 3H). 1-1951 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.88 (d, J = 5.0 Hz, 1H), 7.82 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.65-7.62 (m, 1H), 7.48-7.44 (m, 2H), 7.39-7.35 (m, 2H), 7.32-7.29 (m, 2H), 5.15 (s, 2H), 4.35 (s, 3H). 1-1952 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.72 (d, J = 5.0 Hz, 1H), 7.73-7.70 (m, 2H), 7.63 (dd, J = 7.5, 2.0 Hz, 1H), 7.22 (d, J = 7.5 Hz, 1H), 4.32 (s, 3H), 3.94 (s, 3H), 3.79 (s, 3H). 1-1953 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.31 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.43 (d, J = 2.0 Hz, 1H), 8.32 (dd, J = 7.5, 2.0 Hz, 1H), 7.81 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H). 1-1954 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.46 (s, 1H), 8.25- 8.22 (m, 2H), 7.54 (d, J = 5.0 Hz, 1H), 4.39 (s, 3H). 1-1955 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.17 (d, J = 2.0 Hz, 1H), 8.04 (dd, J = 7.5, 2.0 Hz, 1H), 7.83 (d, J = 7.5 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H). 1-1956 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.09 (d, J = 2.0 Hz, 1H), 8.05 (dd, J = 7.5, 2.0 Hz, 1H), 7.74 (d, J = 7.5 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H). 1-1957 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 8.25 (s, 1H), 7.98 (s, 1H), 7.92 (s, 1H), 7.69 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H). 1-1958 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.18 (dd, J = 7.5, 2.0 Hz, 1H), 8.10 (d, J = 2.0 Hz, 1H), 7.70 (d, J = 7.5 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H). 1-1959 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.32 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.78 (s, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.49 (s, 1H), 7.42 (s, 1H), 4.31 (s, 3H), 3.79 (s, 3H). 1-1960 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.01 (d, J = 2.0 Hz, 1H), 7.79 (dd, J = 7.5, 2.0 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 7.15 (d, J = 7.5 Hz, 1H), 4.39 (s, 3H), 3.85 (s, 3H). 1-1961 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.19 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.44 (dd, J = 7.5, 2.0 Hz, 1H), 7.82 (dd, J = 7.5, 2.0 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.37 (dd, J = 7.5, 7.5 Hz, 1H), 4.34 (s, 3H), 3.84 (s, 3H). 1-1962 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 8.46 (dd, J = 7.5, 2.0 Hz, 1H), 8.34 (d, J = 2.0 Hz, 1H), 7.98 (d, J = 7.5 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H). 1-1963 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.38 (d, J = 2.0 Hz, 1H), 8.11 (dd, J = 7.5, 2.0 Hz, 1H), 7.53 (d, J = 5.0 Hz, 1H), 7.36 (d, J = 7.5 Hz, 1H), 4.34 (s, 3H). 1-1964 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.70 (d, J = 5.0 Hz, 1H), 7.94 (dd, J = 7.5, 2.0 Hz, 1H), 7.87 (d, J = 2.0 Hz, 1H), 7.76 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-1965 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 2.0 Hz, 1H), 7.89 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.43 (d, J = 7.5 Hz, 1H), 4.30 (s, 3H). 1-1966 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.16 (s, 1H), 7.54 (d, J = 5.0 Hz, 1H), 7.28 (s, 1H), 4.35 (s, 3H), 2.37 (s, 3H). 1-1967 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 10.0 Hz, 1H), 7.74 (d, J = 6.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 2.43 (s, 3H). 1-1968 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.87 (s, 2H), 7.49 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-1969 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.64 (d, J = 5.0 Hz, 1H), 7.56-7.53 (m, 1H), 7.00-6.97 (m, 1H), 4.34 (s, 3H), 3.84 (s, 3H). 1-1970 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.71 (d, J = 5.0 Hz, 1H), 7.71 (d, J = 5.0 Hz, 1H), 7.68-7.61 (m, 2H), 4.35 (s, 3H). 1-1971 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.50 (d, J = 5.0 Hz, 1H), 7.36 (s, 2H), 4.31 (s, 3H), 3.82 (s, 6H), 3.73 (s, 3H). 1-1972 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 9.25 (s, 1H), 8.67 (d, J = 5.0 Hz, 1H), 7.86 (dd, J = 7.5, 2.0 Hz, 1H), 7.52 (d, J = 5.0 Hz, 1H), 7.13 (dd, J = 7.5, 2.0 Hz, 1H), 7.01-6.98 (m, 1H), 4.33 (s, 3H). 1-1973 Cl

1-1974 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 7.95 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.60 (s, 1H), 7.28 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.89 (s, 3H). 1-1975 Cl

1-1976 Cl

1-1977 Cl

1-1978 Cl

1-1979 Cl

1-1980 Cl

1-1981 Cl

1-1982 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 8.58 (d, J = 5.0 Hz, 1H), 7.78 (d, J = 5.0 Hz, 1H), 7.63 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 2.60 (s, 3H), 2.21 (s, 3H). 1-1983 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.78 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.64 (s, 2H), 4.39 (s, 3H), 2.55 (s, 6H). 1-1984 Cl

1-1985 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.81 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.18 (s, 1H), 7.87 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 2.32 (s, 3H). 1-1986 Cl

1-1987 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.26 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H), 2.30 (s, 3H). 1-1988 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 8.42 (s, 1H), 8.33 (s, 1H), 7.78 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.28 (s, 3H). 1-1989 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.30 (s, 1H), 8.74 (d, J = 5.0 Hz, 1H), 8.62 (s, 1H), 8.25 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 2.30 (s, 3H). 1-1990 Cl

1-1991 Cl

1-1992 Cl

1-1993 Cl

1-1994 Cl

1-1995 Cl

1-1996 Cl

1-1997 Cl

1-1998 Cl

1-1999 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 6.80 (d, J = 4.5 Hz, 1H), 6.09 (d, J = 4.5 Hz, 1H), 4.35 (s, 3H), 2.35 (s, 3H). 1-2000 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 9.25 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 7.92 (d, J = 5.0 Hz, 1H), 7.67 (s, 1H), 6.88 (s, 1H), 4.33 (s, 3H). 1-2001 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 11.51 (s, 1H), 8.97 (d, J = 5.0 Hz, 1H), 8.04 (d, J = 5.0 Hz, 1H), 7.74-7.71 (m, 2H), 7.33 (d, J = 4.5 Hz, 1H), 6.74 (s, 1H), 2.41 (s, 3H). 1-2002 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.79 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 4.5 Hz, 1H), 7.27 (d, J = 4.5 Hz, 1H), 4.33 (s, 3H), 2.31 (s, 3H). 1-2003 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.93 (d, J = 5.0 Hz, 1H), 8.10 (s, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.68 (s, 1H), 4.33 (s, 3H). 1-2004 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.30 (s, 1H), 8.91 (d, J = 5.0 Hz, 1H), 7.96 (d, J = 5.0 Hz, 1H), 7.85 (s, 1H), 7.42 (d, J = 4.5 Hz, 1H), 7.18 (d, J = 4.5 Hz, 1H), 4.51 (s, 2H), 4.33 (s, 3H), 1.39 (s, 9H). 1-2005 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.94 (d, J = 5.0 Hz, 1H), 7.86-7.78 (m, 2H), 7.60 (d, J = 7.5 Hz, 1H), 7.51-7.45 (m, 3H), 7.34 (d, J = 7.5 Hz, 1H), 4.36 (s, 3H). 1-2006 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 7.72 (d, J = 5.0 Hz, 1H), 7.03 (d, J = 4.5 Hz, 1H), 6.81 (d, J = 4.5 Hz, 1H), 6.35-6.31 (m, 1H), 4.36 (s, 3H). 1-2007 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.74 (d, J = 5.0 Hz, 1H), 7.60 (d, J = 3.5 Hz, 1H), 6.69 (d, J = 3.5 Hz, 1H), 4.60-4.56 (m, 1H), 4.32 (s, 3H), 1.27 (d, J = 7.0 Hz, 6H). 1-2008 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 7.91 (d, J = 4.5 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 7.59 (d, J = 4.5 Hz, 1H), 6.58-6.53 (m, 1H), 4.30 (s, 3H). 1-2009 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 6.14 (s, 1H), 4.32 (s, 3H), 2.75 (s, 3H), 2.24 (s, 3H). 1-2010 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.80 (d, J = 5.0 Hz, 1H), 7.75 (d, J = 5.0 Hz, 1H), 7.67 (dd, J = 7.5, 1.5 Hz, 1H), 7.61 (dd, J = 7.5, 1.5 Hz, 1H), 7.42-7.38 (m, 1H), 7.30- 7.23 (m, 2H), 4.33 (s, 3H). 1-2011 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.92 (d, J = 5.0 Hz, 1H), 8.58-8.56 (m, 1H), 8.49-8.47 (m, 1H), 8.10-8.07 (m, 1H), 8.05-8.02 (m, 1H), 7.83 (d, J = 5.0 Hz, 1H), 7.73-7.69 (m, 1H), 7.57-7.54 (m, 1H), 7.49-7.46 (m, 1H), 4.32 (s, 3H). 1-2012 F CH₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.46 (d, J = 5.0 Hz, 1H), 7.50-7.47 (m, 1H), 4.33 (s, 3H), 2.54 (s, 3H). 1-2013 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.30 (d, J = 5.0 Hz, 1H), 7.82 (dd, J = 7.0, 5.0 Hz, 1H), 4.33 (s, 3H), 1.77-1.72 (m, 1H), 0.84-0.79 (m, 2H), 0.71-0.65 (m, 2H). 1-2014 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.35 (d, J = 5.0 Hz, 1H), 7.81 (dd, J = 7.0, 5.0 Hz, 1H), 4.34 (s, 3H), 3.70 (t, J = 6.0 Hz, 2H), 2.43 (t, J = 7.0 Hz, 2H), 2.09-2.02 (m, 2H). 1-2015 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.95-7.89 (m, 2H), 7.81 (dd, J = 7.0, 5.0 Hz, 1H), 7.51-7.45 (m, 2H), 4.37 (s, 3H). 1-2016 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s 1H), 8.47 (d, J = 5.0 Hz, 1H), 8.18-8.12 (m, 2H), 7.84 (dd, J = 6.0, 5.0 Hz, 1H), 7.77-7.71 (m, 2H), 4.38 (s, 3H). 1-2017 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 9.06 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.31 (d, J = 8.0 H,z 1H), 8.16 (d, J = 5.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 4.34 (s, 3H). 1-2018 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.90 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.09- 8.01 (m, 2H), 7.47 (d, J = 8.0 Hz, 1H), 4.30 (s, 3H). 1-2019 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.73 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.37- 8.28 (m, 2H), 8.07 (d, J = 7.0 Hz, 1H), 4.32 (s, 3H). 1-2020 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.22 (d, J = 5.0 Hz, 1H), 8.09 (dd, J = 7.0, 5.0 Hz, 1H), 7.96 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H). 1-2021 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.33 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.14-8.10 (m, 1H), 7.90 (s, 1H), 7.00 (s, 1H), 4.35 (s, 3H), 3.93 (s, 3H). 1-2022 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 8.05 (dd, J = 7.0, 5.0 Hz, 1H), 7.98-7.62 (m, 2H), 7.04 (s, 1H), 4.35 (s, 3H). 1-2023 OH

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.38 (d, J = 5.0 Hz, 1H), 7.89-7.86 (m, 3H), 7.35- 7.27 (m, 2H), 4.38 (s, 3H). 1-2024 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.75 (d, J = 5.0 Hz, 1H), 8.05 (d, J = 5.0 Hz, 1H), 6.86-6.82 (m, 1H), 6.17-6.13 (m 1H), 5.68-5.64 (m, 1H), 4.32 (s, 3H), 3.79 (s, 3H). 1-2025 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.43 (d, J = 5.0 Hz, 1H), 7.89 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.83 (s, 3H), 1.78-1.74 (m, 1H), 0.84-0.77 (m, 2H), 0.72-0.65 (m, 2H). 1-2026 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.16 (d, J = 5.0 Hz, 1H), 7.88 (s, 1H), 7.03 (s, 1H), 4.32 (s, 3H), 3.93 (s, 3H), 3.82 (s, 3H). 1-2027 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.85 (d, J = 5.0 Hz, 1H), 8.18 (d, J = 5.0 Hz, 1H), 7.62 (d, J = 4.5 Hz, 1H), 7.12 (d, J = 4.5 Hz, 1H), 4.31 (s, 3H), 3.79 (s, 3H), 2.39 (s, 3H). 1-2028 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.30 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.84-7.78 (m, 2H), 7.51-7.42 (m, 3H), 4.35 (s, 3H), 3.68 (s, 3H). 1-2029 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.57 (d, J = 5.0 Hz, 1H), 8.17-8.10 (m, 2H), 7.87 (d, J = 5.0 Hz, 1H), 7.77-7.71 (m, 2H), 4.36 (s, 3H), 3.71 (s, 3H). 1-2030 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 9.06 (s, 1H), 8.73 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.30 (d, J = 8.0 Hz, 1H), 8.18 (d, J = 5.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 4.33 (s, 3H), 3.72 (s, 3H). 1-2031 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.79 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 8.0, Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 4.33 (s, 3H), 3.53 (s, 3H). 1-2032 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.30 (s, 1H), 8.72-8.63 (m, 2H), 8.32 (d, J = 8.0 Hz, 1H), 8.20 (d, J = 9.0 Hz, 1H), 7.65 (d, J = 5.0 Hz, 1H), 4.38 (s, 3H), 3.58 (s, 3H). 1-2033 OMe

1-2034 OMe

1-2035 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.83 (t, J = 57.0 Hz, 1H), 7.70 (s, 1H), 7.58 (d, J = 5.0 H, 1H), 6.96 (s, 1H), 4.33 (s, 3H), 2.59 (s, 3H). 1-2036

1-2037

1-2038

¹H NMR (500 MHz, DMSO-d₆) δ 12.31 (s, 1H), 8.55 (d, J = 5.0 Hz, 1H), 8.12 (d, J = 5.0 Hz, 1H), 6.78 (dd, J = 17.0, 10.0 Hz, 1H), 6.06 (dd, J = 14.0, 10.0 Hz, 1H), 5.95 (s, 1H), 5.58 (dd, J = 17.0, 14.0 Hz, 1H), 4.33 (s, 3H), 2.71 (s, 3H). 1-2039

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.92 (s, 1H), 8.51 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.24 (d, J = 5.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 5.95 (s, 1H), 4.29 (s, 3H), 2.64 (s, 3H). 1-2040

¹H NMR (500 MHz, DMSO-d₆) δ 12.31 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 8.24 (d, J = 5.0 Hz, 1H), 7.75 (s, 1H), 6.87 (s, 1H), 5.95 (s, 1H), 4.38 (s, 3H), 3.92 (s, 3H), 2.72 (s, 3H). 1-2041

CH₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.46 (d, J = 5.0 Hz, 1H), 8.04 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.92 (s, 6H), 2.56 (s, 3H). 1-2042

CH₂CH₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.44 (d, J = 5.0 Hz, 1H), 8.08 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 3.13 (q, J = 8.0 Hz, 2H), 2.89 (s, 6H), 1.18 (t, J = 8.0 Hz, 3H). 1-2043

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 8.17 (d, J = 5.0 Hz, 1H), 6.73 (dd, J = 17.0, 10.0 Hz, 1H), 6.10 (dd, J = 14.0, 10.0 Hz, 1H), 5.60 (dd, J = 17.0, 14.0 Hz, 1H), 4.33 (s, 3H), 2.91 (s, 6H). 1-2044

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.44 (d, J = 5.0 Hz, 1H), 8.01 (d, J = 5.0 Hz, 1H), 7.61-7.54 (m, 2H), 7.24-7.17 (m, 2H), 4.37 (s, 3H), 2.80 (s, 6H). 1-2045

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.88 (s, 1H), 8.54 (d, J = 5.0 Hz, 1H), 8.41 (d, J = 5.0 Hz, 1H), 8.25 (d, J = 5.0 Hz, 1H), 8.15 (d, J = 8.0 Hz, 1H), 7.46 (dd, J = 8.0, 5.0 Hz, 1H), 4.39 (s, 3H), 2.82 (s, 6H). 1-2046

¹H NMR (500 MHz, DMSO-d₆) δ 12.91 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.26 (d, J = 5.0 Hz, 1H), 7.48 (d, J = 7.5 Hz, 1H), 7.10 (d, J = 7.5 Hz, 1H), 4.35 (s, 3H), 2.93 (s, 6H), 2.38 (s, 3H). 1-2047

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.27 (d, J = 5.0 Hz, 1H), 7.70 (s, 1H), 6.82 (s, 1H), 4.33 (s, 3H), 3.92 (s, 3H), 2.95 (s, 6H). 1-2048

¹H NMR (500 MHz, DMSO-d₆) δ 12.33 (s, 1H), 8.68 (d, J = 5.0 Hz, 1H), 8.27 (d, J = 5.0 Hz, 1H), 7.97-7.72 (m, 2H), 6.97 (s, 1H), 4.33 (s, 3H), 2.94 (s, 6H). 1-2049

1-2050

1-2051 SMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.84-7.78 (m, 2H), 7.51-7.42 (m, 3H), 4.37 (s, 3H), 2.48 (s, 3H). 1-2052 SMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.56 (d, J = 5.0 Hz, 1H), 8.11-8.04 (m, 2H), 7.77-7.71 (m, 2H), 7.66 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 2.22 (s, 3H). 1-2053 SMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.89-7.83 (m, 2H), 7.72-7.66 (m, 2H), 7.52 (d, J = 5.0 Hz, 1H), 6.99 (s, 2H), 4.33 (s, 3H), 2.22 (s, 3H). 1-2054 SMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.79 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 4.34 (s, 3H), 2.53 (s, 3H). 1-2055 SMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.69 (d, J = 5.0 Hz, 1H), 8.62 (s, 1H), 8.31 (d, J = 8.0 Hz, 1H), 8.22 (d, J = 6.0 Hz, 1H), 7.59 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.54 (s, 3H). 1-2056 SMe

1-2057 SMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.82 (d, J = 5.0 Hz, 1H), 7.83 (t, J = 57.0 Hz, 1H), 7.70 (s, 1H), 7.58 (d, J = 5.0 Hz, 1H), 6.96 (s, 1H), 4.34 (s, 3H), 2.59 (s, 3H). 1-2058

CH₃

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.87 (d, J = 5.0 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.37 (s, 3H), 2.72 (s, 3H), 2.61 (s, 3H). 1-2059

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.99 (d, J = 5.0 Hz, 1H), 7.88 (d, J = 5.0 Hz, 1H), 6.99 (dd, J = 17.0, 10.0 Hz, 1H), 6.10 (dd, J = 14.0, 10.0 Hz, 1H), 5.72 (dd, J = 17.0, 14.0 Hz, 1H), 4.31 (s, 3H), 2.66 (s, 3H). 1-2060

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 9.09 (d, J = 5.0 Hz, 1H), 7.94 (s, 1H), 7.82 (d, J = 5.0 Hz, 1H), 6.92 (s, 1H), 4.36 (s, 3H), 3.92 (s, 3H), 2.71 (s, 3H). 1-2061 Cl OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.60 (s, 3H). 1-2062 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.06 (d, J = 5.0 Hz, 1H), 7.22 (d, J = 5.0 Hz, 1H), 4.39 (s, 2H), 4.30 (s, 3H). 1-2063 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.17 (d, J = 5.0 Hz, 1H), 7.47-7.39 (m, 2H), 7.32 (d, J = 5.0 Hz, 1H), 7.18-7.11 (m, 2H), 7.00-6.96 (m, 1H), 4.35 (s, 3H). 1-2064 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.08 (d, J = 5.0 Hz, 1H), 7.43-7.27 (m, 5H), 7.22 (d, J = 5.0 Hz, 1H), 5.33 (s, 2H), 4.40 (s, 3H). 1-2065 Cl SMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.20 (s, 1H), 8.65 (d, J = 5.0 Hz, 1H), 7.70 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.60 (s, 3H). 1-2066 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.36 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.10 (t, J = 5.0 Hz, 2H), 1.68-1.64 (m, 2H), 1.02 (t, J = 8.0 Hz, 3H). 1-2067 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 8.47 (d, J = 5.0 Hz, 1H), 7.69 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 1.35 (s, 9H). 1-2068 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.39 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 7.36-7.30 (m, 3H), 7.28-7.21 (m, 2H), 4.55 (s, 2H), 4.33 (s, 3H). 1-2069 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.48 (d, J = 5.0 Hz, 1H), 7.66 (d, J = 5.0 Hz, 1H), 7.17 (d, J = 7.0 Hz, 2H), 7.12-7.06 (m, 2H), 4.53 (s, 2H), 4.39 (s, 3H), 3.51 (s, 3H). 1-2070 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.84 (d, J = 5.0 Hz, 1H), 8.00 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H), 2.83 (t, J = 5.0 Hz, 1H), 2.55 (t, J = 5.0 Hz, 1H), 1.47-1.42 (m, 2H), 0.93 (t, J = 8.0 Hz, 3H). 1-2071 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.96 (d, J = 5.0 Hz, 1H), 8.16 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.13 (t, J = 8.0 Hz, 2H), 1.56- 1.48 (m, 2H), 0.90 (t, J = 8.0 Hz, 3H). 1-2072 Cl NH₂

¹H NMR (500 MHz, DMSO-d₆) δ 12.31 (s, 1H), 8.39 (d, J = 5.0 Hz, 1H), 7.45 (d, J = 5.0 Hz, 1H), 6.30 (s, 2H), 4.33 (s, 3H). 1-2073 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 9.25 (s, 1H), 8.42 (d, J = 5.0 Hz, 1H), 7.44 (d, J = 5.0 Hz, 1H), 4.37 (s, 3H), 3.04 (s, 3H). 1-2074 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.34 (d, J = 5.0 Hz, 1H), 7.40 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.19 (s, 6H). 1-2075 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.31 (s, 1H), 10.22 (s, 1H), 8.41 (d, J = 5.0 Hz, 1H), 7.78- 7.72 (m, 2H), 7.42 (d, J = 5.0 Hz, 1H), 7.33-7.28 (m, 2H), 7.02-6.99 (m, 1H), 4.33 (s, 3H). 1-2076 Cl

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.99 (s, 1H), 8.37 (d, J = 5.0 Hz, 1H), 7.35 (d, J = 5.0 Hz, 1H), 7.21-7.15 (m, 2H), 6.92-6.86 (m, 2H), 4.62 (s, 2H), 4.30 (s, 3H), 3.79 (s, 3H). 1-2077 F OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.83 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H), 3.55 (s, 3H). 1-2078 F

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.66 (d, J = 5.0 Hz, 1H), 8.15 (dd, J = 8.0, 5.0 Hz, 1H), 4.33 (s, 3H), 2.81 (t, J = 5.0 Hz, 1H), 2.54 (t, J = 5.0 Hz, 1H), 1.47-1.41 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H). 1-2079 OMe OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 4.32 (s, 3H), 3.62 (s, 3H), 3.45 (s, 3H). 1-2080 OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.39 (s, 3H), 2.81 (t, J = 5.0 Hz, 1H), 2.54 (t, J = 5.0 Hz, 1H), 1.47-1.41 (m, 2H), 0.93 (t, J = 8.0 Hz, 3H). 1-2081 OMe NH₂

¹H NMR (500 MHz, DMSO-d₆) δ 12.27 (s, 1H), 8.23 (d, J = 5.0 Hz, 1H), 7.61 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 4.21 (s, 2H), 3.81 (s, 3H). 1-2082 SMe OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.24 (s, 1H), 8.02 (d, J = 5.0 Hz, 1H), 7.28 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.92 (s, 3H), 2.31 (s, 3H). 1-2083 SMe SMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.59 (d, J = 5.0 Hz, 1H), 7.38 (d, J = 5.0 Hz, 1H), 4.31 (s, 3H), 2.62 (s, 3H), 2.20 (s, 3H). 1-2084 SMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.33 (s, 1H), 8.77 (d, J = 5.0 Hz, 1H), 7.73 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.85 (t, J = 5.0 Hz, 1H), 2.55 (t, J = 5.0 Hz, 1H), 2.39 (s, 3H), 1.46-1.40 (m, 2H), 0.92 (t, J = 8.0 Hz, 3H). 1-2085

OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.29 (s, 1H), 8.28 (d, J = 5.0 Hz, 1H), 7.14 (d, J = 5.0 Hz, 1H), 4.35 (s, 3H), 3.92 (s, 3H), 2.86 (s, 3H). 1-2086

OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.23 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.34 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 3.95 (s, 3H), 3.24 (s, 3H). 1-2087 NH₂

¹H NMR (500 MHz, DMSO-d₆) δ 12.20 (s, 1H), 8.45 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 5.83 (s, 2H), 4.33 (s, 3H), 2.76 (t, J = 8.0 Hz, 1H), 2.53 (t, J = 8.0 Hz, 1H), 1.47-1.42 (m, 2H), 0.88 (t, J = 8.0 Hz, 3H). 1-2088

¹H NMR (500 MHz, DMSO-d₆) δ 12.21 (s, 1H), 7.98 (d, J = 5.0 Hz, 1H), 7.58 (d, J = 5.0 Hz, 1H), 6.58 (s, 1H), 5.95 (s, 1H), 4.30 (s, 3H), 2.73 (s, 3H), 2.68 (s, 3H). 1-2089

OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.35 (s, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.57 (d, J = 5.0 Hz, 1H), 4.30 (s, 3H), 3.83 (s, 3H), 2.91 (s, 6H). 1-2090

¹H NMR (500 MHz, DMSO-d₆) δ 12.26 (s, 1H), 8.58 (d, J = 5.0 Hz, 1H), 8.28 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.93 (s, 6H), 2.82 (t, J = 5.0 Hz, 1H), 2.54 (t, J = 5.0 Hz, 1H), 1.47-1.41 (m, 2H), 0.92 (t, J = 7.9 Hz, 3H). 1-2091

¹H NMR (500 MHz, DMSO-d₆) δ 12.33 (s, 1H), 8.09 (d, J = 5.0 Hz, 1H), 7.19 (d, J = 5.0 Hz, 1H), 6.50 (s, 1H), 4.36 (s, 3H), 2.81 (s, 6H), 2.73 (s, 3H). 1-2092

¹H NMR (500 MHz, DMSO-d₆) δ 12.28 (s, 1H), 8.19 (d, J = 5.0 Hz, 1H), 7.80 (d, J = 5.0 Hz, 1H), 4.36 (s, 3H), 3.18 (s, 6H), 2.93 (s, 6H). 1-2093

¹H NMR (500 MHz, DMSO-d₆) δ 12.31 (s, 1H), 8.62 (d, J = 5.0 Hz, 1H), 7.87 (d, J = 5.0 Hz, 1H), 7.38-7.32 (m, 2H), 6.92-6.86 (m, 2H), 6.22 (s, 1H), 4.34-4.31 (m, 5H), 3.79 (s, 3H), 2.75 (t, J = 5.0 Hz, 1H), 2.55 (t, J = 5.0 Hz, 1H), 1.50-1.44 (m, 2H), 0.95 (t, J = 8.0 Hz, 3H). 1-2094

OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.25 (s, 1H), 8.63 (d, J = 5.0 Hz, 1H), 7.55 (d, J = 5.0 Hz, 1H), 6.69-6.64 (m, 1H), 5.74-5.70 (m, 1H), 5.46-5.42 (m, 1H), 4.33 (s, 3H), 3.63 (s, 3H). 1-2095

OMe

¹H NMR (500 MHz, DMSO-d₆) δ 12.31 (s, 1H), 8.64 (d, J = 5.0 Hz, 1H), 7.56 (d, J = 5.0 Hz, 1H), 7.23-7.13 (m, 4H), 4.33 (s, 3H), 3.80 (s, 3H). 1-2096

1-2097

¹H NMR (500 MHz, DMSO-d₆) δ 12.22 (s, 1H), 8.60 (d, J = 5.0 Hz, 1H), 8.23 (d, J = 5.0 Hz, 1H), 4.33 (s, 3H), 2.85 (t, J = 8.0 Hz, 1H), 2.65 (t, J = 8.0 Hz, 1H), 2.48 (s, 3H), 2.40 (s, 3H) 1.47-1.41 (m, 2H), 0.91 (t, J = 8.0 Hz, 3H).

The method for preparing the compound of the invention will be explained in detail in the following program and embodiment. The material is commercial available or prepared through known method reported in the literature or shown in the route. Those skilled in the art should understand that the compound of the invention can also be synthesized by other synthetic route. Although the detailed material and reaction condition in the synthetic route have been explicated in the following text, it is still easy to be replaced by other similar material and condition. Isomer of the compound, for example, that produced with the variation of the preparation method of the present invention is included in the scope of the present invention. In addition, the following preparation method can be further modified according to the disclosures of the present invention by using common chemical method known to those skilled in the art, for example, protection of suitable group in the process of the reaction, etc.

The following method of application can be used to improve further understanding of the preparation method of the present invention. The specific material, class and condition have been determined to be further explication of the present invention, not to be any limit of the reasonable scope thereof. Reagents of the following synthetic compound showed in the table can either be purchased from the market or easily prepared by those skilled in the art.

Examples of representative compounds are as follows, the synthetic methods of other compounds are similar, and will not be described in detail here.

1. Synthesis of Compound 1-1

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a, 3.0 equivalents of sodium hydroxide, and 1.2 equivalents of 1-1-1 were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 120° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 1-2 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product 1-1-2 was obtained by reverse-phase purification with yield of 78%.

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-1-2 was charged at room temperature. After dissolved with dichloromethane (10V), 1.1 equivalent of N,N′-carbonyldiimidazole (CDI) was added, and reacted at 30-40° C. for 1 hour under stirring. After stirring, 1.2 equivalent of b and 1.0 equivalent of 1,8-diazabicycloundec-7-ene (DBU) were added, and continued to react at 30-40° C. for 16-24 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added to the reaction system, stirred, extracted, and the organic phase was poured into the waste liquid. The water phase was adjusted to pH 5-6 with 2M hydrochloric acid solution, and a large amount of solid was precipitated out at this time. After stirring for 15-30 minutes, the solid was filtered to obtain the product, and the product was dried to remove water with yield of about 72%.

2. Synthesis of Compound 1-17

It can be prepared by referring to the above method for preparing compound 1-1; or it can be prepared by the following method:

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a was charged at room temperature. After dissolved with dichloromethane (10V), 1.1 equivalent of N,N′-carbonyldiimidazole (CDI) was added, and reacted at 30-40° C. for 1 hour under stirring. After stirring, 1.2 equivalent of b and 1.0 equivalent of 1,8-diazabicycloundec-7-ene (DBU) were added, and continued to react at 30-40° C. for 16-24 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added to the reaction system, stirred, extracted, and the organic phase was poured into the waste liquid. The water phase was adjusted to pH 5-6 with 2M hydrochloric acid solution, and a large amount of solid was precipitated out at this time. After stirring for 15-30 minutes, the solid was filtered to obtain the product, and the product was dried to remove water with yield of about 75%,

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-17-1, 3.0 equivalents of potassium carbonate, and 1.2 equivalents of c were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 110° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 5-6 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product was obtained by reverse-phase purification with yield of 50%.

3. Synthesis of Compounds 1-203 and 1-205

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-203-1 (It can be prepared by referring to the above method for preparing compound 1-17) was charged at room temperature. After dissolved with N,N-dimethylformamide (10V), 1.0 equivalent of sodium thiomethoxide aqueous solution (20% content) was added, and reacted at 50-60° C. for 6-8 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 2% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, and adjusted to pH 5-6 with 2M hydrochloric acid solution, and the solid was precipitated out at this time, the insolubles were removed by filtration. The mother liquor was distilled under reduced pressure to remove the solvent, and the compound 1-203 was obtained by reverse-phase purification with yield of about 62%.

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-203 was charged at room temperature. After dissolved with dichloromethane (10V), 1.0 equivalent of 1-205-1 (85% content) was added, and reacted at 10-20° C. for 15-30 minutes under stirring. The reaction solution was sampled and when the remaining raw materials were less than 1% according to LC-MS detection, the reaction was terminated. After the reaction was completed, sodium thiosulfate aqueous solution was added to quench the reaction, the insolubles were removed by filtration, distilled under reduced pressure to remove the solvent, and the compound 1-205 was obtained by reverse-phase purification with yield of about 50%.

Or

can be prepared from

by referring to the above preparation method, then

can be prepared, and reacts with

respectively to obtain compound 1-203 and compound 1-205 by referring to the synthesis step (2) of the above compound 1-1.

4. Synthesis of Compound 1-223

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a, 3.0 equivalents of sodium hydroxide, and 2.5 equivalents of c were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 120° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 1-2 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product 1-223-1 was obtained by reverse-phase purification with yield of 45%.

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-223-1 was charged at 10-20° C. After dissolved with pyridine (10V), 10% 4-dimethylaminopyridine (DMAP) and 1.2 equivalents of compound b were charged sequentially, and 3.0 equivalents of thionyl chloride was added in a dropwise manner at 10-20° C. under stirring, then heated to 30-40° C., and reacted for 2 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, the pyridine was removed by distillation under reduced pressure, dissolved with 10V water, adjusted to pH 2-3 with 1M hydrochloric acid, then extracted three times with dichloromethane (5V). The organic phases were combined and distilled under reduced pressure to remove the solvent. The product 1-223 was obtained by reverse-phase purification with yield of about 52%.

5. Synthesis of Compound 1-249

It can be prepared by referring to the above method for preparing compound 1-1; or it can be prepared by the following method:

To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-17-1, 3.0 equivalents of potassium carbonate, and 1.2 equivalents of 1-249-1 were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 110° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, and the mother liquor was adjusted to pH 5-6 with 2M hydrochloric acid solution, then extracted three times with ethyl acetate (5V). The organic phases were combined and distilled under reduced pressure to remove ethyl acetate. The product was obtained by reverse-phase purification with yield of 50%.

6. Synthesis of Compound 1-962

(1) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound a, 3.0 equivalents of potassium carbonate, and 1.1 equivalents of c were charged sequentially at room temperature. After dissolved with 10:1 dioxane-water (10V), nitrogen replacement was performed three times under stirring, the catalyst 1,1′-bis(diphenylphosphino)ferrocene dichloride palladium(II) dichloromethane complex (1%) was added, nitrogen replacement was performed three times, then heated to 120° C., and reacted at this temperature for 16-24 hours. The reaction solution was sampled and when the remaining raw materials were less than 1% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added, the insolubles were removed by filtration, extracted two times with ethyl acetate (5V), and the water phases were adjusted to pH 2-3 with 2M hydrochloric acid solution, then the solid was precipitated out, filtered and dried to obtain the product 1-962-1 with yield of 82%.

(2) To a 50 mL single-necked eggplant-shaped flask, 1.0 equivalent of compound 1-962-1 was charged at room temperature. After dissolved with dichloromethane (10V), 1.1 equivalent of N,N′-carbonyldiimidazole (CDI) was added, and reacted at 30-40° C. for 1 hour under stirring. After stirring, 1.2 equivalent of d and 1.0 equivalent of 1,8-diazabicycloundec-7-ene (DBU) were added, and continued to react at 30-40° C. for 5-8 hours under stirring. The reaction solution was sampled and when the remaining raw materials were less than 5% according to LC-MS detection, the reaction was terminated. After the reaction was completed, 10V water was added to the reaction system, stirred, extracted, and the organic phase was poured into the waste liquid. The water phase was adjusted to pH 5-6 with 2M hydrochloric acid solution, and a large amount of solid was precipitated out at this time. After stirring for 15-30 minutes, the solid was filtered to obtain the product, and the product was dried to remove water with yield of about 69%.

Biological Activity Evaluation:

The activity level criteria for plant damage (i.e., growth control rate) are as follows:

Level 5: growth control rate is above 85%;

Level 4: growth control rate is greater than or equal to 60% and less than 85%;

Level 3: growth control rate is greater than or equal to 40% and less than 60%;

Level 2: growth control rate is greater than or equal to 20% and less than 40%;

Level 1: growth control rate is greater than or equal to 5% and less than 20%;

Level 0: growth control rate is less than 5%.

The above growth control rates are fresh weight control rates.

Experiment on weeding effect in post-emergence stage: monocotyledonous and dicotyledonous weed seeds and major crop seeds (wheat, corn, rice, soybean, cotton, oilseed rape, millet, sorghum) were placed in plastic pots filled with soil, then covered with 0.5-2 cm of soil, allowed to grow in a good greenhouse environment. After 2 weeks of sowing, the test plants were treated in the 2-3 leaf stage. The tested compounds of the present invention were respectively dissolved in acetone at the dosage of 2000, 1000, 500, 250, 125 g/ha, then added with Tween 80 and 1.5 liter/ha of emulsifiable concentrate of methyl oleate as synergist, diluted with a certain amount of water to obtain a solution with a certain concentration, and sprayed with a spray tower onto the plants. After the application, the plants were cultured for 3 weeks in the greenhouse, and then the experimental results were listed in Table 1.

TABLE 1 Results on weeding effect in post-emergence stage Com- Descurainia Abutilon Amaranthus Chenopodium pound No. sophia theophrasti retroflexus L. album 1-1 5 5 5 5 1-2 5 5 5 5 1-3 5 5 5 5 1-4 5 5 5 5 1-5 5 5 5 5 1-6 5 5 5 5 1-7 5 5 5 5 1-8 5 5 5 5 1-9 5 5 5 5 1-10 5 5 5 5 1-11 5 5 5 5 1-12 5 5 5 5 1-13 5 5 5 5 1-14 5 5 5 5 1-15 5 5 5 5 1-16 5 5 5 5 1-17 5 5 5 5 1-18 5 5 5 5 1-19 5 5 5 5 1-20 5 5 5 5 1-21 5 5 5 5 1-22 5 5 5 5 1-23 5 5 5 5 1-24 5 5 5 5 1-25 5 5 5 5 1-26 5 5 5 5 1-27 5 5 5 5 1-28 5 5 5 5 1-29 5 5 5 5 1-30 5 5 5 5 1-31 5 5 5 5 1-32 5 5 5 5 1-33 5 5 5 5 1-34 5 5 5 5 1-35 5 5 5 5 1-36 5 5 5 5 1-37 5 5 5 5 1-38 5 5 5 5 1-39 5 5 5 5 1-40 5 5 5 5 1-41 5 5 5 5 1-42 5 5 5 5 1-43 5 5 5 5 1-44 5 5 5 5 1-45 5 5 5 5 1-46 5 5 5 5 1-47 5 5 5 5 1-48 5 5 5 5 1-49 5 5 5 5 1-50 5 5 5 5 1-51 5 5 5 5 1-52 5 5 5 5 1-53 5 5 5 5 1-54 5 5 5 5 1-55 5 5 5 5 1-56 5 5 5 5 1-57 5 5 5 5 1-58 5 5 5 5 1-59 5 5 5 5 1-60 5 5 5 5 1-61 5 5 5 5 1-62 5 5 5 5 1-63 5 5 5 5 1-64 5 5 5 5 1-65 5 5 5 5 1-66 5 5 5 5 1-67 5 5 5 5 1-68 5 5 5 5 1-69 5 5 5 5 1-70 5 5 5 5 1-71 5 5 5 5 1-72 5 5 5 5 1-73 5 5 5 5 1-74 5 5 5 5 1-75 5 5 5 5 1-76 5 5 5 5 1-77 5 5 5 5 1-78 5 5 5 5 1-79 5 5 5 5 1-80 5 5 5 5 1-81 5 5 5 5 1-82 5 5 5 5 1-83 5 5 5 5 1-84 5 5 5 5 1-85 5 5 5 5 1-86 5 5 5 5 1-87 5 5 5 5 1-88 5 5 5 5 1-89 5 5 5 5 1-90 5 5 5 5 1-91 5 5 5 5 1-92 5 5 5 5 1-93 5 5 5 5 1-94 5 5 5 5 1-95 5 5 5 5 1-96 5 5 5 5 1-97 5 5 5 5 1-98 5 5 5 5 1-99 5 5 5 5 1-100 5 5 5 5 1-101 5 5 5 5 1-102 5 5 5 5 1-103 5 5 5 5 1-104 5 5 5 5 1-105 5 5 5 5 1-106 5 5 5 5 1-107 5 5 5 5 1-108 5 5 5 5 1-109 5 5 5 5 1-110 5 5 5 5 1-111 5 5 5 5 1-112 5 5 5 5 1-113 5 5 5 5 1-114 5 5 5 5 1-115 5 5 5 5 1-116 5 5 5 5 1-117 5 5 5 5 1-118 5 5 5 5 1-119 5 5 5 5 1-120 5 5 5 5 1-121 5 5 5 5 1-122 5 5 5 5 1-123 5 5 5 5 1-124 5 5 5 5 1-125 5 5 5 5 1-126 5 5 5 5 1-127 5 5 5 5 1-128 5 5 5 5 1-129 5 5 5 5 1-130 5 5 5 5 1-131 5 5 5 5 1-132 5 5 5 5 1-133 5 5 5 5 1-134 5 5 5 5 1-135 5 5 5 5 1-136 5 5 5 5 1-137 5 5 5 5 1-138 5 5 5 5 1-139 5 5 5 5 1-140 5 5 5 5 1-141 5 5 5 5 1-142 5 5 5 5 1-143 5 5 5 5 1-144 5 5 5 5 1-145 5 5 5 5 1-146 5 5 5 5 1-147 5 5 5 5 1-148 5 5 5 5 1-149 5 5 5 5 1-150 5 5 5 5 1-151 5 5 5 5 1-152 5 5 5 5 1-153 5 5 5 5 1-154 5 5 5 5 1-155 5 5 5 5 1-156 5 5 5 5 1-157 5 5 5 5 1-158 5 5 5 5 1-159 5 5 5 5 1-160 5 5 5 5 1-161 5 5 5 5 1-162 5 5 5 5 1-163 5 5 5 5 1-164 5 5 5 5 1-165 5 5 5 5 1-166 5 5 5 5 1-167 5 5 5 5 1-168 5 5 5 5 1-169 5 5 5 5 1-170 5 5 5 5 1-171 5 5 5 5 1-172 5 5 5 5 1-173 5 5 5 5 1-174 5 5 5 5 1-175 5 5 5 5 1-176 5 5 5 5 1-177 5 5 5 5 1-178 5 5 5 5 1-179 5 5 5 5 1-180 5 5 5 5 1-181 5 5 5 5 1-182 5 5 5 5 1-183 5 5 5 5 1-184 5 5 5 5 1-185 5 5 5 5 1-186 5 5 5 5 1-187 5 5 5 5 1-188 5 5 5 5 1-189 5 5 5 5 1-190 5 5 5 5 1-191 5 5 5 5 1-192 5 5 5 5 1-193 5 5 5 5 1-194 5 5 5 5 1-195 5 5 5 5 1-196 5 5 5 5 1-197 5 5 5 5 1-198 5 5 5 5 1-199 5 5 5 5 1-200 5 5 5 5 1-201 5 5 5 5 1-202 5 5 5 5 1-203 5 5 5 5 1-204 5 5 5 5 1-205 5 5 5 5 1-206 5 5 5 5 1-207 5 5 5 5 1-208 5 5 5 5 1-209 5 5 5 5 1-210 5 5 5 5 1-211 5 5 5 5 1-212 5 5 5 5 1-213 5 5 5 5 1-214 5 5 5 5 1-215 5 5 5 5 1-216 5 5 5 5 1-217 5 5 5 5 1-218 5 5 5 5 1-219 5 5 5 5 1-220 5 5 5 5 1-221 5 5 5 5 1-222 5 5 5 5 1-223 5 5 5 5 1-228 5 5 5 5 1-229 5 5 5 5 1-230 5 5 5 5 1-233 5 5 5 5 1-234 5 5 5 5 1-249 5 5 5 5 1-307 5 5 5 5 1-334 5 5 5 5 1-650 5 5 5 5 1-962 5 5 5 5 1-1257 5 5 5 5 1-1286 5 5 5 5 1-1577 5 5 5 5 1-1607 5 5 5 5 1-1918 5 5 5 5 1-1925 5 5 5 5 1-1972 5 5 5 5 1-2004 5 5 5 5 1-2006 5 5 5 5 1-2010 5 5 5 5 1-2016 5 5 5 5 1-2029 5 5 5 5 1-2044 5 5 5 5 1-2052 5 5 5 5 1-2053 5 5 5 5 1-2061 5 5 5 5 1-2062 5 5 5 5 1-2063 5 5 5 5 1-2064 5 5 5 5 1-2065 5 5 5 5 1-2069 5 5 5 5 1-2070 5 5 5 5 1-2071 5 5 5 5 1-2075 5 5 5 5 Note: The application dose was active ingredient 2000 g/ha.

In addition, under the active ingredient of 250 g/ha, many compounds also show good crop selectivity and excellent control effect on key weeds. For example, see Table 2:

TABLE 2 Test results Alopecurus Beckmannia Alopecurus Sclerochloa Descurainia No. aequalis syzigachne myosuroides dura sophia Wheat 1-15 5 5 5 5 5 0 1-17 5 5 5 5 5 0 Control 0 0 0 0 0 0 compound A

Control Compound A:

Experiment on Weed Effect in Pre-Emergence Stage

Seeds of monocotyledonous and dicotyledonous weeds and main crops (e.g. wheat, corn, rice, soybean, cotton, oilseed rape, millet and sorghum) were put into a plastic pot loaded with soil and covered with 0.5-2 cm soil. The test compounds of the present invention was dissolved with acetone, then added with tween 80, diluted by a certain amount of water to reach a certain concentration, and sprayed immediately after sowing. The obtained seeds were incubated for 4 weeks in the greenhouse after spraying and the test results were observed. It was observed that the herbicide mostly had excellent effect at the application rate of 2000 g a.i./ha, especially to weeds such as Echinochloa crusgalli, Digitaria sanguinalis, Abutilon theophrasti, etc. And many compounds had good selectivity for corn, wheat, rice, soybean, oilseed rape, etc.

It is indicated from the experiment that the compounds of the present invention generally have good weed control efficacy, especially for the major cyperaceae weeds like Echinochloa crusgalli, Digitaria sanguinalis, and Setaria viridis, etc., and the major broad-leaved weeds like Abutilon theophrasti, Rorippa indica, and Bidens pilosa L., etc., which are widely occurring in corn, rice, and wheat fields, and have excellent commercial value. Above all, it is noted that they have extremely high activity to weeds, which are resistant to ALS inhibitor, like Rorippa indica, Descurainia sophia, Capsella bursa-pastoris, Lithospermum arvense, Galium aparine L., Stellaria media, Setaria viridis, Echinochloa crusgalli, Digitaria sanguinalis, Alopecurus aequalis, Beckmannia syzigachne, etc.

Transplanted rice safety evaluation and weed control effect evaluation in rice field:

Rice field soil was loaded into a 1/1,000,000 ha pot. The seeds of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Sagittaria trifolia, and Monochoria vaginalis were sowed and gently covered with soil, then left to stand still in greenhouse in the state of 0.5-1 cm of water storage. The tuber of Sagittaria trifolia was planted in the next day or 2 days later. It was kept at 3-4 cm of water storage thereafter. The weeds were treated by dripping the WP or SC water diluents prepared according to the common preparation method of the compounds of the present invention with pipette homogeneously to achieve specified effective amount when Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., and Monochoria vaginalis reached 0.5 leaf stage and Sagittaria trifolia reached the time point of primary leaf stage.

In addition, the rice field soil that loaded into the 1/1,000,000 ha pot was leveled to keep water storage at 3-4 cm depth. The 3 leaf stage rice (japonica rice) was transplanted at 3 cm of transplanting depth the next day. The compound of the present invention was treated by the same way after 5 days of transplantation.

The fertility condition of Echinochloa crusgalli, Scirpus juncoides, Bidens tripartita L., Sagittaria trifolia and Monochoria vaginalis 14 days after the treatment of the compound of the invention and the fertility condition of rice 21 days after the treatment of the compound of the invention respectively with the naked eye. Evaluate the weed control effect with the above 0-5 activity standard level, many compounds show excellent activity and selectivity. Wherein, the seeds of Echinochloa crusgali, Scirpus juncoides, Bidens tripartita, Sagittaria trifolia and Monochoria vaginalis were collected from Heilongjiang Province of China. The tests indicated that the weeds were resistant to the common doses of Pyrazosulfuron-ethyl and Penoxsulam.

It could be seen from this experiment that the compound of the present invention has excellent activity against the anti-ALS weeds which is a serious challenge in the production, and could solve the increasingly serious problem of resistance.

At the same time, it is found after several tests that the compound of the present invention and its composition have good selectivity to many gramineae grass such as Zoysia japonica, bermuda grass, tall fescue, bluegrass, ryegrass and seashore paspalum etc, and is able to control many important grass weeds and broadleaf weeds. The compound also shows excellent selectivity and commercial value in the tests on wheat, corn, rice, sugarcane, soybean, cotton, oil sunflower, potato, orchards and vegetables in different herbicide application methods. 

1. A 4-pyridinyl formamide compound or derivative thereof, as shown in Formula I:

Wherein, X, and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, or cycloalkenylalkyl, which is with or without halogen; OR¹, COR¹, COOR¹, OCOR¹, OCOOR¹, NR³SO₂R², OSO₂R², S(O)_(m)R², NR³COR¹, NR³COOR¹, C(O)NR³OR¹, SO₂OR¹, C(O)NR⁴R⁵, NR³C(O)NR⁴R⁵, OC(O)NR⁴R⁵, SO₂NR⁴R⁵, C(S)R¹, C(S)OR¹, C(S)SR², C(O)SR², SC(O)R¹, SC(S)R¹, OC(S)R¹, -alkyl-C(S)R¹, -alkyl-C(S)OR¹, -alkyl-C(O)SR¹, -alkyl-C(S)SR¹, -alkyl-SC(O)R¹, -alkyl-OC(S)R¹, -alkyl-SC(S)R¹, —O-alkyl-NR⁴R⁵, —S-alkyl-NR⁴R⁵, -alkyl-O-alkyl-NR⁴R⁵, -alkyl-S-alkyl-NR⁴R⁵, -alkyl-(C═S)n-NR⁴R⁵, —NH-alkyl-NR⁴R⁵, -alkyl-OR¹, -alkyl-COR¹, -alkyl-CO₂R¹, -alkyl-OCOR¹, -alkyl-NR³COR¹, -alkyl-SO₂OR¹, -alkyl-NR³SQ₂R², -alkyl-OSO₂R², -alkyl-S(O)_(m)R², -alkyl-CONR⁴R⁵, -alkyl-SO₂NR⁴R⁵, NR⁴R⁵,

P(O)(OR⁶)₂, CH₂P(O)(OR⁶)₂, SO₂NR⁴R⁵-alkyl-S(O)_(m)R², -alkyl-CN, -alkylaryl, -alkylheteroaryl, -alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl; R¹, R³, R⁴, and R⁵ each independently represent hydrogen, aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, halogenated alkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkyl, halogenated cycloalkyl, alkoxyalkyl, or cycloalkylalkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and alkoxyalkoxycarbonyl; R² represents aryl, arylalkyl, heteroaryl, heteroarylalkyl, alkyl, alkenyl, alkynyl, cycloalkyl, or cycloalkylalkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and alkoxyalkoxycarbonyl; R⁶ represents methyl, or ethyl; R⁷, and R⁸ each independently represent hydrogen, alkyl, alkenyl, or alkynyl; R⁹ represents alkyl, alkenyl, or alkynyl; M represents

which is unsubstituted or substituted; R₁₁ represents hydrogen, halogen, cyano, nitro, alkyl which is unsubstituted or substituted with a substituent selected from R₁₃, cycloalkyl which is unsubstituted or substituted with a substituent selected from R₁₄, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, NH₂, aminoacyl, carboxyl, alkoxyalkoxycarbonyl, OR₁₅, -alkyl-OR₁₅, C(O)R₁₆, -alkyl-C(O)R₁₆, C(O)OR₁₆, -alkyl-C(O)OR₁₆, S(O)_(m)R₁₆, -alkyl-S(O)_(m)R₁₆, —N(R₁₆)₂, —NHR₁₆, —C(O)NHR₁₆, —C(O)N(R₁₆)₂, —NHC(O)R₁₇, heterocyclyl, heterocyclylalkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, arylalkyl, aryloxy, arylcarbonyl, heteroaryl, heteroarylalkyl, heteroaryloxy, or heteroarylcarbonyl; R₁₂ represents hydrogen, alkyl which is unsubstituted or substituted with a substituent selected from R₁₈, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylalkyl, aryl, or arylalkyl; when M is

—(CH₂)₄— or —CH═CH—CH═CH— formed by R₁₁ and R₁₂, the nitrogen atom bound to R₁₂ and the carbon atom bound to R₁₁ together form a 6-membered ring; R₁₅ represents alkyl which is unsubstituted or substituted with a substituent selected from R₂₁, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, or phenyl; R₁₆ represents alkyl, halogenated alkyl, cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl; R₂₁ represents halogen, cyano, cycloalkyl, hydroxy, mercapto, alkoxy, C(O)R₂₂, carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, —S(O)_(m)-alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with one or more groups selected from R₂₃; R₁₇, and R₂₂ each independently represent hydrogen, alkyl, or N(R₂₄)R₂₅; R₂₃ represents halogen, cyano, nitro, alkyl, alkyl which is unsubstituted or substituted with a substituent selected from R₃₁, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, alkylcarbonyl, cycloalkylcarbonyl, halogenated alkylcarbonyl, halogenated cycloalkylcarbonyl, alkoxycarbonyl, halogenated alkoxycarbonyl, alkylaminocarbonyl, halogenated alkylaminocarbonyl, bis(alkyl)aminocarbonyl, OR₃₂, S(O)_(m)R₃₃, alkylaminosulfonyl, bis(alkyl)aminosulfonyl, NH₂, alkylamino, bis(alkyl)amino, aryl, heteroaryl, or heterocyclyl; R₂₄, and R₂₅ each independently represent hydrogen, alkyl, or phenyl; or, alkylidene chain formed by R₂₄ and R₂₅, and the nitrogen atom(s) bound to R₂₄ and R₂₅ together form a 3-7-membered ring, said alkylidene chain optionally contains one O, S, S(O), S(O)₂, NH, or N-alkyl and optionally substituted by oxo or thio group; R₁₃, R₁₄, R₁₈, and R₃₁ each independently represent halogen, cyano, nitro, carboxyl, alkoxycarbonyl, alkoxyalkoxycarbonyl, S(O)_(m)R₄₁, OR₄₂, aryl, heteroaryl, or heterocyclyl; R₃₂ represents hydrogen, alkyl, halogenated alkyl, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl; R₃₃ represents alkyl, halogenated alkyl, cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, or cycloalkenyl; R₄₁, and R₄₂ each independently represent hydrogen, alkyl, halogenated alkyl, cycloalkyl, halogenated cycloalkyl, alkenyl, halogenated alkenyl, alkynyl, halogenated alkynyl, cycloalkenyl, or phenyl; r represents 1 or 2; m represents 0, 1 or 2; n represents 0, or 1; s represents 0, 1, 2 or
 3. 2. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X, and Y each independently represent nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkyl-C1-C6 alkyl, or C3-C8 cycloalkenyl-C1-C6 alkyl, which is with or without halogen; OR¹, COR¹, COOR¹, OCOR¹, OCOOR¹, NR³SO₂R², OSO₂R², S(O)_(m)R², NR³COR¹, NR³COOR¹, C(O)NR³OR¹, SO₂OR¹, C(O)NR⁴R⁵, NR³C(O)NR⁴R⁵, OC(O)NR⁴R⁵, SO₂NR⁴R⁵, C(S)R¹, C(S)OR¹, C(S)SR², C(O)SR², SC(O)R¹, SC(S)R¹, OC(S)R¹, —(C1-C6)alkyl-C(S)R¹, —(C1-C6)alkyl-C(S)OR¹, —(C1-C6)alkyl-C(O)SR¹, —(C1-C6)alkyl-C(S)SR¹, —(C1-C6)alkyl-SC(O)R¹, —(C1-C6)alkyl-OC(S)R₁, —(C1-C6)alkyl-SC(S)R¹, —O—(C1-C6)alkyl-NR⁴R⁵, —S—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-O—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-S—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-(C═S)_(n)—NR⁴R⁵, —NH—(C1-C6)alkyl-NR⁴R⁵, —(C1-C6)alkyl-OR¹, —(C1-C6)alkyl-COR¹, —(C1-C6)alkyl-CO₂R¹, —(C1-C6)alkyl-OCOR¹, —(C1-C6)alkyl-NR³COR¹, —(C1-C6)alkyl-SO₂OR¹, —(C1-C6)alkyl-NR³SO₂R², —(C1-C6)alkyl-OSO₂R², -alkyl-S(O)_(m)R², —(C1-C6)alkyl-CONR⁴R⁵, —(C1-C6)alkyl-SO₂NR⁴R⁵, NR⁴R⁵,

P(O)(OR⁶)₂, CH₂P(O)(OR⁶)₂, SO₂NR⁴R⁵—(C1-C6)alkyl-S(O)_(m)R², —(C1-C6)alkyl-CN, —(C1-C6)alkylaryl, —(C1-C6)alkylheteroaryl, —(C1-C6)alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl; R¹, R³, R⁴, and R⁵ each independently represent hydrogen, aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkoxy-C1-C6 alkyl, or C3-C8 cycloalkyl-C1-C6 alkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C8 alkoxy-C1-C6 alkoxycarbonyl; R² represents aryl, aryl-C1-C6 alkyl, heteroaryl, heteroaryl-C1-C6 alkyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, or C3-C8 cycloalkyl-C1-C6 alkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C8 alkoxy-C1-C6 alkoxycarbonyl; R⁶ represents methyl, or ethyl; R⁷, and R⁸ each independently represent hydrogen, C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; R⁹ represents C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 alkynyl; M represents

which is unsubstituted or substituted; R₁₁ represents hydrogen, halogen, cyano, nitro, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₁₃, C3-C8 cycloalkyl which is unsubstituted or substituted with a substituent selected from R₁₄, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, NH₂, aminoacyl, carboxyl, C1-C8 alkoxy-C1-C6 alkoxycarbonyl, OR₁₅, —(C1-C6)alkyl-OR₁₅, C(O)R₁₆, —(C1-C6)alkyl-C(O)R₁₆, C(O)OR₁₆, —(C1-C6)alkyl-C(O)OR₁₆, S(O)_(m)R₁₆, —(C1-C6)alkyl-S(O)_(m)R₁₆, —N(R₁₆)₂, —NHR₁₆, —C(O)NHR₁₆, —C(O)N(R₁₆)₂, —NHC(O)R₁₇, heterocyclyl, heterocyclyl-C1-C6 alkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, aryl-C1-C6 alkyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryl-C1-C6 alkyl, heteroaryloxy, or heteroarylcarbonyl; R₁₂ represents hydrogen, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₁₈, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, C1-C8 alkoxy-C1-C6 alkyl, C1-C8 alkylthio-C1-C6 alkyl, C1-C8 alkoxycarbonyl-C1-C6 alkyl, aryl, or aryl-C1-C6 alkyl; when M is

—(CH₂)₄— or —CH═CH—CH═CH— formed by R₁₁ and R-12, the nitrogen atom bound to R₁₂ and the carbon atom bound to R₁₁ together form a 6-membered ring; R₁₅ represents C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₂₁, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or phenyl; R₁₆ represents C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl; R₂₁ represents halogen, cyano, C3-C8 cycloalkyl, hydroxy, mercapto, C1-C8 alkoxy, C(O)R₂₂, carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy-C1-C6 alkoxycarbonyl, —S(O)_(m)—(C1-C8)alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with one or more groups selected from R₂₃; R₁₇, and R₂₂ each independently represent hydrogen, C1-C8 alkyl, or N(R₂₄)R₂₅; R₂₃ represents halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkyl which is unsubstituted or substituted with a substituent selected from R₃₁, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, C1-C8 alkylcarbonyl, C3-C8 cycloalkylcarbonyl, halogenated C1-C8 alkylcarbonyl, halogenated C3-C8 cycloalkylcarbonyl, C1-C8 alkoxycarbonyl, halogenated C1-C8 alkoxycarbonyl, C1-C8 alkylaminocarbonyl, halogenated C1-C8 alkylaminocarbonyl, bis(C1-C8 alkyl)aminocarbonyl, OR₃₂, S(O)_(m)R₃₃, C1-C8 alkylaminosulfonyl, bis(C1-C8 alkyl)aminosulfonyl, NH₂, C1-C8 alkylamino, bis(C1-C8 alkyl)amino, aryl, heteroaryl, or heterocyclyl; R₂₄, and R₂₅ each independently represent hydrogen, C1-C8 alkyl, or phenyl; or, C2-C8 alkylidene chain formed by R₂₄ and R₂₅, and the nitrogen atom(s) bound to R₂₄ and R₂₅ together form a 3-7-membered ring, said C2-C8 alkylidene chain optionally contains one O, S, S(O), S(O)₂, NH, or N-alkyl and optionally substituted by oxo or thio group; R₁₃, R₁₄, R₁₈, and R₃₁ each independently represent halogen, cyano, nitro, carboxyl, C1-C8 alkoxycarbonyl, C1-C8 alkoxy-C1-C8 alkoxycarbonyl, S(O)_(m)R₄₁, OR₄₂, aryl, heteroaryl, or heterocyclyl; R₃₂ represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl; R₃₃ represents C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, or C3-C8 cycloalkenyl; R₄₁, and R₄₂ each independently represent hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 alkynyl, halogenated C2-C8 alkynyl, C3-C8 cycloalkenyl, or phenyl; r represents 1, or 2; m represents 0, 1, or 2; n represents 0, or 1; s represents 0, 1, 2, or 3; wherein, the “heterocyclyl” is

which has 0, 1, or 2 oxo groups; the “aryl” is phenyl, naphthyl,

the “heteroaryl” is

the above-mentioned groups are respectively unsubstituted or substituted by at least one group selected from: halogen, nitro, cyano, thiocyano, cyanoalkyl, mercapto, hydroxy, hydroxyalkyl, carboxyl, formyl, trialkylsilyl, dialkylphosphonyl; heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted; alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkyl substituted by alkyl, OR″, SR″, -alkyl-OR″, —O— alkyl-OR″, -alkyl-SR″, COR″, -alkyl-COR″, —O-alkyl-COR″, COOR″, -alkyl-COOR″, —O— alkyl-COOR″, COSR″, SOR″, SO₂R″, —O—SO₂R″, -alkyl-SO₂R″, OCOR″, -alkyl-OCOR″, or SCOR″ group, which is with or without halogen; and amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, or aminosulfonyl group which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO₂R″, and OR″, wherein the R″, COR″, COOR″, SO₂R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O— or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O— or —CH═CH—CH═CH— group is with or without halogen; R″ each independently represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl; or heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, heteroaryl, or heteroarylalkyl, which is unsubstituted or substituted.
 3. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X represents nitro, halogen, cyano, formyl, thiocyano, mercapto; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C3 alkyl, or C3-C6 cycloalkenyl-C1-C3 alkyl, which is with or without halogen; OR¹, COR¹, COOR¹, OCOR¹, OCOOR¹, NR³SO₂R², OSO₂R², S(O)_(m)R², NR³COR¹, NR³COOR¹, C(O)NR³OR¹, SO₂OR¹, C(O)NR⁴R⁵, NR³C(O)NR⁴R⁵, OC(O)NR⁴R⁵, SO₂NR⁴R⁵, C(S)R¹, C(S)OR¹, C(S)SR², C(O)SR², SC(O)R¹, SC(S)R¹, OC(S)R¹, —(C1-C3)alkyl-C(S)R¹, —(C1-C3)alkyl-C(S)OR¹, —(C1-C3)alkyl-C(O)SR¹, —(C1-C3)alkyl-C(S)SR¹, —(C1-C3)alkyl-SC(O)R¹, —(C1-C3)alkyl-OC(S)R¹, —(C1-C3)alkyl-SC(S)R¹, —O—(C1-C3)alkyl-NR⁴R⁵, —S—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-O—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-S—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-(C═S)_(n)—NR⁴R⁵, —NH—(C1-C3)alkyl-NR⁴R⁵, —(C1-C3)alkyl-OR¹, —(C1-C3)alkyl-COR¹, —(C1-C3)alkyl-CO₂R¹, —(C1-C3)alkyl-OCOR¹, —(C1-C3)alkyl-NR³COR¹, —(C1-C3)alkyl-SO₂OR¹, —(C1-C3)alkyl-NR³SO₂R², —(C1-C3)alkyl-OSO₂R², -alkyl-S(O)_(m)R², —(C1-C3)alkyl-CONR⁴R⁵, —(C1-C3)alkyl-SO₂NR⁴R⁵, NR⁴R⁵,

P(O)(OR⁶)₂, CH₂P(O)(OR⁶)₂, SO₂NR⁴R⁵—(C1-C3)alkyl-S(O)_(m)R², —(C1-C3)alkyl-CN, —(C1-C3)alkylaryl, —(C1-C3)alkylheteroaryl, —(C1-C3)alkylheterocyclyl, aryl, heteroaryl, or heterocyclyl; Y represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkenyl, which is with or without halogen; OR¹, S(O)_(m)R², NR⁴R⁵, heterocyclyl, aryl, or heteroaryl; R¹, R³, R⁴, and R⁵ each independently represent hydrogen, aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, or C3-C6 cycloalkyl-C1-C3 alkyl, wherein the last 10 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C6 alkoxy-C1-C3 alkoxycarbonyl; R² represents aryl, aryl-C1-C3 alkyl, heteroaryl, heteroaryl-C1-C3 alkyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkyl-C1-C3 alkyl, wherein the last 5 groups as mentioned are each substituted by s groups selected from the group consisting of cyano, halogen, nitro, thiocyano, OR⁷, S(O)_(m)R⁹, NR⁷R⁸, NR⁸OR⁷, COR⁷, OCOR⁷, SCOR⁷, NR⁸COR⁷, CO₂R⁷, COSR⁷, CONR⁷R⁸, and C1-C6 alkoxy-C1-C3 alkoxycarbonyl; R⁶ represents methyl, or ethyl; R⁷, and R⁸ each independently represent hydrogen, C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; R⁹ represents C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl; M represents

which is unsubstituted or substituted; R₁₁ represents hydrogen, halogen, cyano, nitro, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₁₃, C3-C6 cycloalkyl which is unsubstituted or substituted with a substituent selected from R₁₄, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, NH₂, aminoacyl, carboxyl, C1-C6 alkoxy-C1-C3 alkoxycarbonyl, OR₁₅, —(C1-C3)alkyl-OR₁₅, C(O)R₁₆, —(C1-C3)alkyl-C(O)R₁₆, C(O)OR₁₆, —(C1-C3)alkyl-C(O)OR₁₆, S(O)_(m)R₁₆, —(C1-C3)alkyl-S(O)_(m)R₁₆, —N(R₁₆)₂, —NHR₁₆, —C(O)NHR₁₆, —C(O)N(R₁₆)₂, —NHC(O)R₁₇, heterocyclyl, heterocyclyl-C1-C3 alkyl, heterocyclyloxy, heterocyclylcarbonyl, aryl, aryl-C1-C3 alkyl, aryloxy, arylcarbonyl, heteroaryl, heteroaryl-C1-C3 alkyl, heteroaryloxy, or heteroarylcarbonyl; R₁₂ represents hydrogen, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₁₈, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl, aryl, or aryl-C1-C3 alkyl; when M is

—(CH₂)₄— or —CH═CH—CH═CH— formed by R₁₁ and R₁₂, the nitrogen atom bound to R₁₂ and the carbon atom bound to R₁₁ together form a 6-membered ring; R₁₅ represents C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₂₁, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, or phenyl; R₁₆ represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl; R₂₁ represents halogen, cyano, C3-C6 cycloalkyl, hydroxy, mercapto, C1-C6 alkoxy, C(O)R₂₂, carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C3 alkoxycarbonyl, —S(O)_(m)—(C1-C6)alkyl, heteroaryl, heterocyclyl, or phenyl which is unsubstituted or substituted with 1˜3 groups selected from R₂₃; R₁₇, and R₂₂ each independently represent hydrogen, C1-C6 alkyl, or N(R₂₄)R₂₅; R₂₃ represents halogen, cyano, nitro, C1-C6 alkyl, C1-C6 alkyl which is unsubstituted or substituted with a substituent selected from R₃₁, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, C1-C6 alkylcarbonyl, C3-C6 cycloalkylcarbonyl, halogenated C1-C6 alkylcarbonyl, halogenated C3-C6 cycloalkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkylaminocarbonyl, halogenated C1-C6 alkylaminocarbonyl, bis(C1-C6 alkyl)aminocarbonyl, OR₃₂, S(O)_(m)R₃₃, C1-C6 alkylaminosulfonyl, bis(C1-C6 alkyl)aminosulfonyl, NH₂, C1-C6 alkylamino, bis(C1-C6 alkyl)amino, aryl, heteroaryl, or heterocyclyl; R₂₄, and R₂₅ each independently represent hydrogen, C1-C6 alkyl, or phenyl; or, C2-C6 alkylidene chain formed by R₂₄ and R₂₅, and the nitrogen atom(s) bound to R₂₄ and R₂₅ together form a 3-7-membered ring, said C2-C6 alkylidene chain optionally contains one O, S, S(O), S(O)₂, NH, or N-alkyl and optionally substituted by oxo or thio group; R₁₃, R₁₄, R₁₈, and R₃₁ each independently represent halogen, cyano, nitro, carboxyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C6 alkoxycarbonyl, S(O)_(m)R₄₁, OR₄₂, aryl, heteroaryl, or heterocyclyl; R₃₂ represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl; R₃₃ represents C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, or C3-C6 cycloalkenyl; R₄₁, and R₄₂ each independently represent hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 alkynyl, halogenated C2-C6 alkynyl, C3-C6 cycloalkenyl, or phenyl; r represents 1, or 2; m represents 0, 1, or 2; n represents 0, or 1; s represents 0, 1, 2, or 3; wherein, the “heterocyclyl” is

which has 0, 1, or 2 oxo groups; the “aryl” is phenyl, naphthyl,

the “heteroaryl” is

the above-mentioned groups are respectively unsubstituted or substituted by 1˜3 groups selected from: halogen, nitro, cyano, thiocyano, cyano C1-C6 alkyl, mercapto, hydroxy, hydroxy C1-C6 alkyl, carboxyl, formyl;

phenyl, or benzyl group, which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxycarbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkyl substituted by C1-C6 alkyl, OR″, SR″, —(C1-C6) alkyl —OR″, —O—(C1-C6) alkyl —OR″, —(C1-C6) alkyl —SR″, COR″, —(C1-C6) alkyl —COR″, —O—(C1-C6) alkyl —COR″, COOR″, —(C1-C6) alkyl —COOR″, —O—(C1-C6) alkyl —COOR″, COSR″, SOR″, SO₂R″, —O—SO₂R″, —(C1-C6) alkyl —SO₂R″, OCOR″, —(C1-C6) alkyl —OCOR″, or SCOR″ group, which is with or without halogen; and amino, aminoalkyl, aminocarbonyl, or aminosulfonyl group, which is unsubstituted or substituted by one or two groups selected from R″, COR″, COOR″, SO₂R″, and OR″, wherein the R″, COR″, COOR″, SO₂R″, or OR″ is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group is with or without halogen; R′ each independently represents hydrogen, nitro, hydroxy, amino; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkyl-C1-C6 alkyl,

C1-C6 alkoxy, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C3-C6 cycloalkyloxy, C1-C6 alkoxy-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthiocarbonyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl-C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylcarbonyl-C1-C6 alkyl, C1-C6 alkylacyloxy, C1-C6 alkylamino, C1-C6 alkylaminocarbonyl, C1-C6 alkoxyaminocarbonyl, C1-C6 alkoxycarbonyl-C1-C6 alkyl, C1-C6 alkylaminocarbonyl-C1-C6 alkyl, tri(C1-C6 alkyl)silyl, or di(C1-C6 alkyl)phosphonyl, which is with or without halogen; or phenyl, or benzyl which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxycarbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen; R″ each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, C3-C6 cycloalkenyl; or

phenyl, or benzyl which is unsubstituted or substituted by 1˜3 groups selected from halogen, hydroxy, nitro, cyano, amino, carboxyl, C1-C6 alkyl with or without halogen, C2-C6 alkenyl with or without halogen, C2-C6 alkynyl with or without halogen, C3-C6 cycloalkyl with or without halogen, C1-C6 alkoxy with or without halogen, C1-C6 alkoxycarbonyl with or without halogen, C1-C6 alkylacyl with or without halogen, C1-C6 alkylacyloxy with or without halogen, C1-C6 alkylamino with or without halogen, and C1-C6 alkylsulfonyl with or without halogen.
 4. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X represents halogen, nitro, cyano, OR¹, S(O)_(m)R², NR³COR¹, NR⁴R⁵,

C1-C6 alkoxy-C1-C3 alkyl; C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or C3-C6 cycloalkyl, which is with or without halogen;

or phenyl which is unsubstituted or substituted with 1,2, or 3 groups selected from halogen, and C1-C6 alkoxy; Y represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, or C3-C6 cycloalkenyl, which is with or without halogen; OR¹, S(O)_(m)R², NR⁴R⁵, heterocyclyl, aryl, or heteroaryl; R¹, R³, R⁴, and R⁵ each independently represent hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl; or benzyl which is unsubstituted or substituted with 1, 2, or 3 groups selected from halogen, and C1-C6 alkoxy; R² represents C1-C6 alkyl, or halogenated C1-C6 alkyl; M represents

which is unsubstituted or substituted; R₁₁ represents hydrogen, C1-C6 alkyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, halogen, C1-C6 alkylamino, bis(C1-C6 alkyl)amino, cyano, nitro, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl, aminocarbonyl, C1-C6 alkylcarbonylamino, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkylsulfinyl-C1-C3 alkyl, C1-C6 alkylsulfonyl-C1-C3 alkyl; or benzyl, phenoxy, benzoyl, pyridyl,

which is unsubstituted or substituted with 1,2, or 3 groups selected from halogen, and C1-C6 alkoxy; R₁₂ represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkoxycarbonyl-C1-C3 alkyl; or phenyl, or benzyl which is unsubstituted or substituted with at least one group selected from halogen, and halogenated C1-C6 alkyl; r represents 1, or 2; m represents 0, 1, or 2; wherein, the “heterocyclyl” is

the “aryl” is phenyl, naphthyl, or

which is unsubstituted or substituted; the “heteroaryl” is

which is unsubstituted or substituted; the aforementioned “substituted” respectively refers to being substituted by 1˜3 groups selected from: halogen, nitro, cyano, thiocyano, cyano C1-C3 alkyl, hydroxy, hydroxy C1-C3 alkyl, mercapto, carboxyl, formyl,

phenyl, phenyl substituted by C1-C6 alkyl, phenoxy, benzyloxy; amino, aminoalkyl, or aminocarbonyl group which is unsubstituted or substituted by one or two groups selected from C1-C6 alkyl, COR″, and COOR″; and C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, C1-C6 alkoxy-C1-C3 alkyl, C1-C6 alkylthio-C1-C3 alkyl, C1-C6 alkylcarbonylthio, C3-C6 cycloalkyl substituted with C1-C6 alkyl, OR″, SR″, SOR″, COR″, COOR″, or SO₂R″, which is with or without halogen; or, two adjacent substitutable positions of the above-mentioned “heterocyclyl”, “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group, which is with or without halogen; R′ each independently represents hydrogen, C1-C6 alkyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkyl,

C1-C6 alkoxycarbonyl, C1-C6 alkoxy-C1-C3 alkyl, or benzyl; R″ each independently represents C1-C6 alkyl, or C2-C6 alkenyl; wherein, when X is fluorine, Y is not amino, monomethylamino, monoethylamino and monopropylamino; when M is

X and Y are not methyl at the same time.
 5. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is characterized in that, X represents chlorine, fluorine, bromine, methyl, ethyl, isopropyl, vinyl, allyl, ethynyl, cyclopropyl, trifluoromethyl,

hydroxy, methoxy, ethyloxy, methylthio, ethylthio,

nitro, cyano, methylsulfinyl, ethylsulfinyl, methylsulfonyl, amino, monomethylamino, dimethylamino, acetamido,

phenyl, phenoxy, or 4-fluorophenyl; Y represents methyl, ethyl, vinyl, methoxy,

phenoxy, benzyloxy, methylthio, propylthio, tert-butylthio, benzylthio, 4-methoxybenzylthiol, propylsulfinyl, amino, monomethylamino, dimethylamino, anilino, p-methoxybenzylamino, tert-butyl, cyclopropyl, cyclohexyl,

heterocyclyl, aryl, or heteroaryl; M represents

which is unsubstituted or substituted; R₁₁ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, monochloromethyl, trifluoromethyl, methoxy, isopropyloxy, methylthio, fluorine, chlorine, bromine, iodine, dimethylamino, ethylamino, cyano, nitro, acetyl, methoxycarbonyl; phenyl which is unsubstituted or substituted by 1,2, or 3 groups selected from chlorine, and methoxy; pyridyl,

R₁₂ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, allyl,

or phenyl, or benzyl which is unsubstituted or substituted by 1,2, or 3 groups selected from chlorine, and trifluoromethyl; r represents 1, or 2; wherein, the “heterocyclyl” is

the “aryl” is phenyl, naphthyl, or

which is unsubstituted or substituted; the “heteroaryl”

which is unsubstituted or substituted; the aforementioned “substituted” refers to being substituted by 1,2, or 3 groups selected from: methyl, ethyl, isopropyl, n-butyl, tert-butyl, n-pentyl, vinyl, cyclopropyl,

fluorine, chlorine, bromine, iodine, monobromomethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, butoxy, trifluoromethoxy, hydroxyl, hydroxymethyl, amino, cyano, cyanomethyl, thiocyano, mercapto, nitro, carboxy, formyl, acetyl, methoxycarbonyl, tert-butyloxycarbonyl, methylthio, isopropylthio, methylsulfinyl, methylsulfonyl,

dimethylamino, aminocarbonyl, dimethylaminocarbonyl, acetylamino,

phenyl, 4-ethylphenyl, phenoxy, and benzyloxy; or, two adjacent substitutable positions of the above-mentioned “aryl”, “heteroaryl” groups are linked with —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group to form a ring, wherein the —OCH₂CH₂—, —OCH₂O—, —OCH₂CH₂O—, or —CH═CH—CH═CH— group is with or without halogen; R′ each independently represents hydrogen, methyl, ethyl, n-propyl, isopropyl, difluoromethyl, 3,3,3-trifluoroethyl, benzyl,

wherein, when X is fluorine, Y is not amino and monomethylamino; when M is

X and Y are not methyl at the same time. 6.-10. (canceled)
 11. The 4-pyridinyl formamide compound or derivative thereof according to claim 1, which is selected from the compounds of formula I as listed in Table A1.
 12. A method for preparing the 4-pyridinyl formamide compound of claim 1, comprising subjecting the compound of formula II and the compound of formula III to an amidation reaction to obtain the compound of formula I as follows:

wherein the reaction is carried out in the presence of a halogenating agent, a catalyst and a solvent; or wherein the reaction is carried out in the presence of a condensing agent and a solvent.
 13. The method of claim 12, wherein the reaction is carried out in the presence of SOCl₂ as the halogenating agent, 4-dimethylaminopyridine as the catalyst, and pyridine as the solvent.
 14. The method of claim 12, wherein the reaction is carried out in the presence of CDI, DCC, DBU, or a combination thereof as the condensing agent, and methylene chloride as the solvent.
 15. A herbicidal composition, comprising (i) the 4-pyridinyl formamide compound or derivative thereof of claim 1; optionally further comprising (ii) at least one additional herbicide and/or safener, and/or (iii) at least one agrochemically acceptable formulation auxiliary.
 16. A method for controlling a weed, comprising applying a herbicidally effective amount of at least one 4-pyridinyl formamide compound or derivative thereof of claim 1 on a plant or in a weed area.
 17. A method for preventing and/or controlling a weed in a useful crop, comprising applying at least one 4-pyridinyl formamide compound or derivative thereof of claim 1 on the useful crop or in a weed area.
 18. The method of claim 17, wherein the useful crop is a transgenic crop, or a crop treated by gene editing technique.
 19. A method for controlling a weed, comprising applying a herbicidally effective amount of at least one herbicidal composition of claim 15 on a plant or in a weed area.
 20. A method for preventing and/or controlling a weed in a useful crop, comprising applying at least one herbicidal composition of claim 15 on the useful crop or in a weed area.
 21. The method of claim 20, wherein the useful crop is a transgenic crop, or a crop treated by gene editing technique. 